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Compendium of Organic Synthetic Methods [Vol 4] by L. Wade

By L. Wade

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JOC Related Methods: Section 39 43, 155 (1978) Carboxylic Acids from Esters - Section 23, P r o t e c t i o n o f Alcohols - Section 45A Alcohols and Phenols from Ethers and Epoxides 6 Me3Si C1 NaI * 6 JOC 44, 1247 (1979) 90% 40 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 C6Hl -0Me 1 )Me3Si I * 2 ) H20 ‘sHl SECTION 39 95% 1OH JOC 42, 3761 (1977) A1 Br3 98% A1 Br3 EtSH @OH OH 78% Chem L e t t , 97 (1979) Ph-OMe I2 ,PhSiMe3 * Ph-OH Synthesis, 417 (1977) 9 0% SECTION 39 ALCOHOLS AND PHENOLS FROM ETHERS AND EPOXIDES wcN OMe 41 OH i 1 NaCN ~ 79% DMSO T e t r L e t t , 5183 (1978) Ar-OEt BBr3 CH2C1 * Ar-OH 64-91 % Synth Corn 9, 407 (1979) Jq cycl ohexene Ph-CH2/ A1 C1 ,Pd/C * HO cholestanol Synthesis, 825 (1978) 1 ) Me3SiC1, NaI Ph-O-CH2Ph 2 ) H20 * PhOH t PhCH21 JCS Chem Corn, 874 (1978) 81 % 42 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 qHl7 (rakN* SECTION 39 electrochemical oxidation 95% ‘sHl 70H MeCN/CH2C1 Me Angew I n t Ed 17.

Compendium of Organic Synthetic Methods, Volume4 Edited by Leroy G. Wade, Jr. Copyright 0 1980 by John Wiley & Sons, Inc. CHAPTER 3 PREPARATION OF ALCOHOLS AND PHENOLS Section 31 Alcohols from Acetylenes hv OH JACS 99, 5192 (1977) Section 32 Alcohols from Carboxylic Acids and Acid Halides JCS Chem Comm, 330 (1978) “3 NaBH4 CH3( CH2)14-C-O-N CH3 ( CH2), 4-CH20H 0 Chem L e t t , 981 (1979) 28 69% SECTION 34 ALCOHOLS FROM ALDEHYDES 0 U MeO-CCH2CH2CC1 NaBH4- A1 203 0 II MeO-C-CH 2CH2 CH2 OH 29 80% Synthesis, 912 (1979) Also v i a : Section 33 Esters ( S e c t i o n 38) Alcohols from Alcohols No a d d i t i o n a l examples S e c t i o n 34 n-C5H1,-CH0 Alcohols from Aldehydes Na2S204 ~ n -C5H1 CH20H 63% H20/di oxane Synthesis, 246 (1977) n-C H CHO 9 19 2-propanol a1 umi na n-C H CH OH 919 2 JOC 42, 1202 (1977) 84% 30 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 SECTION 34 ,CH20H CHO I NaH/t-AmONa - 98 % JOC 43, 4804 (1978) Bu3SnH CH3 ( CH2 )6CH0 CH3 ( CH2)&H20H s i l i c a gel 90% JOC 43, 3977 (1978) CH3( CH2)7CH0 Cp2Zr (C1 )BH4 + CH3(CH2)8-OH 90% T e t r L e t t , 4985 (1978) 87% Synthesis, 891 (1978) ALCOHOLS FROM ALDEHYDES SECTION 34 31 BH3 -SMe2 CH20H Ph 82% Ph - JOC 43, 1829 (1978) C5H11-CHO 9 - BBN a py r id ine * CgH1 -CH20H 100% - JOC 42, 4169 (1977) C6H1 3CH0 (HA1 N - i -Pr)6 * CgH13CH20H 98% Z Chem 17, 18 (1977) Ph-CHO MgH2 + P h -CH20H 100% JOC 43, 1557 (1978) PhCH=CHCHO H2 ,co _____I) RhCl PhCH=CH-CH20H BCS Japan 50, 2148 (1977) 83 % 32 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 4 9-BBN Ph-CHZCH-CHO Ph-CH=CH-CH20H SECTION 34 86% JOC 42, 1197 (1977) 100% Chem L e t t , 1085 (1977) C6H1 3-CH0 H2 w C6H13CH20H 88% RuCl ( CO) 2L2 J Organometal Chem 145, 189 (1978) R-CHO IrH3L3,HOAc * R-CH20H Ketones a r e n o t reduced.

Soluble i n organic solve n ts , and UV-active a l l o w i n g f a c i e d e t e c t i o n on TLC. T e t r L e t t , 103 Review: (1 977) " A c t i v a t i o n and P r o t e c t i o n o f t h e Carboxyl Group" Chem & I n d , 610 (1979) Rev ew: " P r o t e c t i n g Groups n Peptide Synthesis" Chem & Ind, 617 (1979) Other r e a c t i o n s useful f o r t h e p r o t e c t i o n o f c a r b o x y l i c a c i d s a r e i n cluded i n Section 107 (Esters from Carboxylic Acids and Acid H a lides) and Section 23 (C a rb o x y l i c Acids from E s t e r s ) .

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