Compendium of Organic Synthetic Methods, Volume 9. Michael B.

Smith
Copyright 2001 by John Wiley & Sons, Inc.
ISBNs: 0-471-14579-3 (Hardback); 0-471-22822-2 (Electronic)

Section 17 Acids from Acids

CHAPTER 2
PREPARATION OF ACID DERIVATIVES

SECTION 16: ACID DERIVATIVES FROM ALKYNES

NO ADDITIONAL EXAMPLES

SECTION 17: ACID DERIVATIVES FROM ACID DERIVATIVES

C02H
HaG,, @b,
A HO

A BuLi, THF-HMPA
+
I * 6
OTs
v
Jv d
OMe
Me0 Me0
(10 1) 82% .
Kusumoto.T.; Ichikawa, S.; Asaka, K.; Sato, K.; Hiyama, T. Tekhedron Lett., 1995, 36, 1071

C02H KF , microwave, 4 min

0
OAc
C02H
< - ti
94% O
Villemin. D,; Labiad, B.; Loupy, A. Synth. Commun.,1993, 23, 419
6 Compendium of Organic Synthetic Methods, Vo19 Section 22

SECTION 18: ACID DERIVATIVES FROM ALCOHOLS AND

THIOLS

02, Pb(OAc)p3 H@ , Pd-C , lh

w lCH20H w w lCH20H 90%
NaOH , H20,15O*C
&@a. M; Nakano, S.; Sugiyama, T.; Tchitoh, K.; Nakao, H.; Akita, M.; More-Oh Y, BUZZ.
Chem. Sot. Jpn., 1993, 66, 15 11

TMS
1. PhI(OAck , AcOH
rt, 8h
w HOgg
2. H20
B 92%
Kirihara, M.; Yokoyama, S.; Kakuda, H.; Momose. T, Tetrahedron Lett., 1995, 36,6907

SECTION 19: ACID DERIVATIVES FROM ALDEHYDES

H202, HCO,H
PhCHO t PhC02H 93%
Dodd. R&; Le Hyaric, M. Synthesis, 1993, 295

NaClO2, aq. MeCN

phmCHo 10C + rt
a ph-co2H

93%
Babu, B.R.; Balasubramanlan.. K.K. Org. Prep. Proceed. Int., 1994, 26, 123

NaN3-MnO$SiC14, CH$$ , O*C 0

PhCHO *
89%
N3
Elmorsv. SS. Tetrahedron Lett., 1995, 36, 1341

SECTION 20: ACID DERIVATIVES FROM ALKYLS,

METHYLENES AND ARYLS

NO ADDITIONAL EXAMPLES

SECTION 21: ACID DERIVATIVES FROM AMIDES

NO ADDITIONAL EXAMPLES

SECTION 22: ACID DERIVATIVES FROM AMINES

NO ADDITIONAL EXAMPLES
Section 25 Acids from Halides

SECTION 23: ACID DERIVATIVES FROM ESTERS

Other reactions useful for the hydrolysis of esters may be found in Section 30A
(Protection of Carboxylic Acids).

0
Et2m3
Ph--CO$Ie w
68%
Rawal.V.H,; Zhong, H.M. Tetrahedron Lett., 1994, 35, 4947

1.2 eq.KOWAliquat , microwave

PhC02Me w PhC02H
2. HCl
Loupy. A,; Pigeon,P.; Ramdani,M.; Jacquault,P. Synth. Commun., 1994, 24, 159

CO (3 atm),8% PPh3
96h, rt
PhMOCHO * PhMCOzH
2% Pd2(dba)$HC13
, toluene
92%(E only)
mote. 4. Bull. Chem. Sot. Jpn., 1995, 68, 433

SECTION 24: ACID DERIVATIVES FROM ETHERS,

EPOXIDES AND THIOETHERS
1. 10%[Bi(mandelate)&O
Ph DMSO , 80C,30 min, air
* Ph-COOH 60%
2. H30+
Zevaco, T.; Dufiach,E.; Postel.M, Tetrahedron Lett., 1993, 34, 2601

C02H
AgBQ , AlC13, MeCN

reflux ,0.35h
02N 02N
. . H; Mohammadpoor-Baltork, 95%
irouzabadl. I. Synth. Cornmun., 1994, 24, 1065

SECTION 25: ACID DERIVATIVES FROM HALIDES AND

SULFONATES

C02, H2, 150C, Id

Me1 * MeC02H
Ni(cod)2+ C%(C0)8
muoka. A; Gotoh, N.; Kobayashi,N.; Hirano,M.; I(omiva. S, Chem. Lett., 1995, 567
 Compendium of Organic Synthetic Methods, Vo19 Section 29

REVIEW:
PreparationOf Thiol Acids,Thiol EstersAnd AmidesBy Reactions Of CarbonylSulfides
With GrignardReagents, &&itzky. A&; Moutou,J.-L.; Yang, 2. Org. Prep. Proceed. Int.,
1995, 27, 361

SECTION 26: ACID DERIVATIVES FROM HYDRIDES

NO ADDITIONAL EXAMPLES

SECTION 27: ACID DERIVATIVES FROM KETONES

Yw
& Cl Nag033/2 H202, 60C

3h

D.T.C,; Cao, Y.H.; Kabalka,G.W. Synth. Commun., 1995, 25, 3695

c C02H

C02H
86%

SECTION 28: ACID DERIVATIVES FROM NITRILES

NO ADDITIONAL EXAMPLES

SECTION 29: ACID DERIVATIVES FROM ALKENES

Fe(CO)5,KOH , CO (1 atm)
H20/iPrOH, 55OC,4d
\
Ph * p4zH xC02,,

(96 . 4) 45%
Brunet.J.-J,; Neibecker,D.; Srivastava,R.S. Tetrahedron L&t., 1993,. 34, 2759

0
HC02H, CO(6.8 atm), DME

*
Pd(OAc)2- dppb, 150C, 16h wco2H 86%
El Ali. B,; Alper, H. J. Org. Chem., 1993, 58, 3595

HCOOH,6.8 atmCO
10%Pd/C, dppb, DME C02H
Ph
5c ph/\/co2H +
\ 150C, Id PhA
(76 . 24) 65%
El Ali. B,; Vasapollo,G.; Alner. H, J. Org. Chem., 1993, 58, 4739
Section 30A Protection of Acids

C6H13
cat. 0~04, Jones reagent
* C6H13-C02H
85%
\ acetone, rt
Henry, J.R.; Webeb. S .pvt J. Org. Chem., 1993, 58, 4745

Pd/C , dppb , PPh3 , CO

u HCOOH ,DME * Eco2

60%
Vasapollo, G.; Somasunderam, A.; El Ali, B.; Blper. H, Tetrahedron Len., 1994, 35, 6203

02 ,2% Co(acac)3 , THF

PhCH=CH2 w PhC02H + PhCHO
70C, Id
(86 14) 99%
Reetz M.T,; Tollner, K. Tetrahedron Lett., 1995, 36, 9461

SECTION 30: ACID DERIVATIVES FROM MISCELLANEOUS

COMPOUNDS
1. 0.1% Na2[PdC14] , CO , Hz0
Nag03 , 40C ,6.5h
PhI02 * PhCOOH 71%
2. H30+
Grushin, V.V.; Alter. H, J. Org. Chem., 1993, 58, 4794

SECTION 30A: PROTECTION OF CARBOXYLIC ACID

DERIVATIVES

A&
5 TBAF@xH20
Ph 5BnSH
* PhCOOH +
P
Ph
0 82% quant
ueki. M,; Aoki, H.; Katoh, T. Tetrahedron Lett., 1993, 34,2783

acidic Al203 ,7 min C02H

QPh microwave , CH2C12, rt 92%

0
Yanna. R&; Chatterjee,AK; Varma, M, TetrahedronLett., 1993, 34,4603
10 Compendium of Organic Synthetic Methods, Vol9 Section 30A

P COzH
12, cyclohexane , rt

cossV,; Albouy, A.; Scheloske, M.; Gomez Pardo, D. Tetrahedron L&t., 1994, 3.5, 1539

1% TFA in CH2C12 ,5 min , rt

ematowicz, MS,; Chao, H.-G.; Matsueda, G.R. Tetrahedron Lett., 1994, 35, 1651

CuC12, 02, aq. DMF

Ph-C02H
phod ph 1 45%
-R.N.; Singh, L. Tetrahedron Lett., 1995, 36, 5401

1. NBS, (Bz0)2, CC14 , heat

Tco2Bn 2. H20 - r3:

m. M&; Montana, J.G. Synlett, 1994, 219

REVIEW:
Recent Developments in Chemical Deprotection of Ester Functional Groups, Salomon,
C.J.; Mata, E.G.; Mascaretti, O.A. Tetrahedron, 1993, 49, 3691

Other reactions useful for the protection of carboxylic acids are included in
Section 107 (Esters from Carboxylic Acids and Acid Halides) and Section 23
(Carboxylic Acids from Esters).