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By Anatoly Bezkorovainy

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Page 48-49 .. .. .. 2. 2loctane EtOH H20 2 pH 2 JOC (1973) Me 38 3224 OCHzCH=CH2 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 2 50 ROH NaH PhCH2Br CgHg SECTION 45A ROCH2Ph w 4 H2 EtOH Pd-C JACS (1971) 93 1746 +- Cleavage o f benzyl ethers with Ph3C BF3 JCS Perkin I (1972) 542 Further examples of the cleavage o f benzyl ethers a r e included in Section 39 (Alcohols and Phenols from Ethers and Epoxides) % PhCH20CH2 0 t-Bu ClSiMe2 imidazole * THF OH t - BuqN F THF o r HOAc H20 t-Bu (More stable than OSiMej.

Tetrahydropyranyl e t h e r s , a c e t a l s a n d o r t h o e s t e r s . . page 48-49 .. .. .. 2. 2loctane EtOH H20 2 pH 2 JOC (1973) Me 38 3224 OCHzCH=CH2 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 2 50 ROH NaH PhCH2Br CgHg SECTION 45A ROCH2Ph w 4 H2 EtOH Pd-C JACS (1971) 93 1746 +- Cleavage o f benzyl ethers with Ph3C BF3 JCS Perkin I (1972) 542 Further examples of the cleavage o f benzyl ethers a r e included in Section 39 (Alcohols and Phenols from Ethers and Epoxides) % PhCH20CH2 0 t-Bu ClSiMe2 imidazole * THF OH t - BuqN F THF o r HOAc H20 t-Bu (More stable than OSiMej.

42-45 . H20 JACS (1967) R2CO BuBr Li THF t R2COH Bu 561 (One-step procedure) JCS P e r k i n I (1972) 1655 57% Chem Corn (1971) 351 53% Ber (1972) 105 1978 42 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 2 SECTION 42 -68% Tetr Lett (1972) 4605 @ @ -" t - . Et20* b C H C H 2 0 H 2 NaOH H202 NaH Me2SO JACS (1972) 0 94 4 2 4 1 OH 1 Li NH3 THF 2 PhCOONa Tetr Lett (1971) 1853 K-graphite - OH THF Can J Chem (1972) PhCO I Me NaAl (OCH2CH20Me)2H2 . 4CS (1971) 93 2897 OH ,@Jc o ~ ~ ~ ~ 2 0 NaBH4-CaC12 H ' P NO2 EtOH ,@ ~HFHCH~OH NO2 Ber (1960) 3 387 NHAc 70% 44 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 2 JACS (1971) SECTION 42 93 7319 Me LiB(hHEt)3H THF + 100% JACS (1972) R2CO R ' 2 S n H 2 or R ' 3 S n H (99% c i s ) 94 7159 R2CHOH S y n t h e s i s (1970) 499 [MeHsio]~ bis ( d i b u t y l a c e t o x y t i n ) t-Bu R2CO EtOH IrCl4 i-PrOH (Me0)3P e t H20 65% OH t-Bu JOC (1973) HC1 0 2 162 R2CHOH Org Synth (1970) 13 + C9H19p Me y 2 NH2=CS02- EtOH H 2 0 NaOH c CgH1gFHOH Me 74% T e t r L e t t (1972) 343 JCS P e r k i n I (1973) 2633 Related methods: Also via: Section 43 45 ALCOHOLS FROM OLEFINS SECTION 44 Alcohols from Aldehydes (section 34) Section 332 302 Olefinic alcohols Acetylenic alcohols Alcohols and Phenols from Nitriles 0000000000000000000000000000000000 No examples Section 44 Alcohols from Olefins 000000000000000000000 for the preparation o f diols from olefins see section 323 (Alcohol-Alcohol) 75% 3 (CF3C0)20 4 H202 NaOH Chem Comm (1971) 1048 H20 JACS (1971) J O C (1973) AlH3 THF 2 CO (70 atmos) 93 2070 38 3968 CSu-t w 60% Synthesis (1972) 197 EtCH=CH2 1 B2Hg THF * 2 Br2 hV CH2C12 H20 3 H202 NaOH H20 76% (EtCH2CH2)2FOH EtCH2 JACS (1971) 93 1 0 2 5 Synthesis (1972) 699 COMPENDIUM OF ORGANIC SYNTHETIC METHODS VOL 2 46 1 B2Hg THF MezC=CHMe 3 Brp H2°2 hv Me Me2CHFOH b 2 MeOH CH2C12 Synthesis (1972) 303 304 699 H2° 1 BugB hv p - x y l e n e 8 2% Me2CHCHMe H20 EtoH NaoH C6H6 2 H202 base * 80% Tetrahedron (1973) 1 BH2Cl 29 2365 EtpO 2 NaOH H202 EtOH H20 * QMe OH JOC (1973) Me SECTION 45 38 182 1 NOCl 2 NaBH4 i-PrOH H20 Aust J Chem (1971) S e c t i o n 45 PhCH=CHCH20H 24 1089 A l c o h o l s f r o m M i s c e l l a n e o u s Compounds 0000D00000000000000000Do00000000000000 H2 nickel boride EtOH * Ph( CH2)30H J O C (1971) a 2018 100% 47 PROTECTION OF ALCOHOLS AND PHENOLS SECTION 45A OH MeOH HO li JOC (1971) @QJs03H 2 2730 NaOH Me _L M e 280-300" Ber (1925) 58B 1211 JACS (1949) 21 3889 Ph2S MeCOCH2K K NH3 * I JACS (1972) Me Electrolysis Et CH2 S e c t i o n 45A 71 % PhCH2CHOH dioxane MeOH t Me4N OTs 94 683 - * 47% JACS (1971) Me 2 5284 P r o t e c t i o n o f Alcohols and Phenols OOOOOOOoOOOOOOOOOOOOooaooooooooooo E s t e r s o f o r g a n i c and inorganic a c i d s .

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