Download Compendium of Organic Synthetic Methods Volume 1 by Ian T. Harrison PDF

By Ian T. Harrison

Offers artificial chemists with a mode for quick retrieval of data from the literature, directory fabric by means of response style instead of through writer identify or ebook date. every one up-to-date quantity will current the newest man made tools for coaching of monofunctional and difunctional compounds. The association is logical and straightforward to keep on with; sections are prepared in accordance with the prospective interconversions among the foremost sensible teams. allows man made chemists to maintain abreast of contemporary advancements and retrieve a selected piece of data speedy and simply.

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Extra info for Compendium of Organic Synthetic Methods Volume 1

Example text

Zn FOOH HC1 (YH2)4 FHMe H20 46% Et y42 CHMe it PhCH2C1 * MeOH (;H2I4 t-Bu JACS ( 1 9 5 0 ) Br fOOH g JACS ( 1 9 4 4 ) 66 46 PhCH2(CH2)5COOH Ber ( 1 9 5 2 ) 6 1 1061 69% COMPENDIUM 48 OF ORGANIC SYNTHETIC METHODS JACS (1948) SECTION 25 2 3352 n glycol J O C (1958) CgH1 gYHCH2Br Me 1 Mg Et20 * QCHO ocl- CgH19yHCH2( CH2)4COOH EtpO 2 P h y s i o l Chem (1951) 3 co2 1 NaCH(S02Et)z 2 CH2'CHCN KOH t - B u O H * 287 65 (CH2)2COOH 2 CH2=CH2 PhCH2C1 584 Me 3 HC1 E t O H 4 N2H4 KOH 1 Li 23 JACS (1969) 47% 91 6362 "zEt I 1 HC1 H 2 0 PhCH2CCH2CH2CN v PhCH2(CH2)3COOH I HOAc "zEt 2 N i NaOH H20 JACS (1952) 74 1225 CARBOXYLIC A C I D S AND A C I D HALIDES FROM HALIDES SECTION 25 BuBr MeCOCH2COOEt t NaOEt KOH H20 BuFHCOOEt COMe 49 BuCH~COOH Org Synth (1941) C o l l Vol 1 248 JACS (1930) 5005 52 1 Mg THF 62% 3 BrCH2COOEt 4 NaOH 1 CH3CODBu-t C8H171 JOC (1968) NaNH2 NH3 + 2 HC1 H20 d i o x a n e 2 CgH17CH2CDOH g JACS (1959) PhCH2C1 1 EtCHzCOOBu-t 2 HC1 NaNH2 NH3 H20 d i o x a n e 1675 * 70% 5817 PhCHZfHCOOH 92% Et 81 5817 JACS (1959) F u r t h e r examples o f t h e a l k y l a t i o n o f e s t e r s w i t h h a l i d e s a r e i n c l u d e d i n s e c t i o n 113 ( E s t e r s f r o m E s t e r s ) .

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U 2 EtI 35 t 50% 262 PhFHCOOH i-Pr Et2O 93% 2 262 C5H117COOH Bu J O C (1967) PhCH2COOH 1397 C5H11 FHCOOH Bu J O C (1970) PhCHzCOOH 86% I JACS (1970) C5H11 CH2COOH 21 2 2797 PhfHCOOH Et B u l l SOC C h i m F r (1964) 2000 88% SECTION 1 7 COMPENDIUM OF ORGANIC SYNTHETIC METHODS 22 COOH 1 (i-Pr)zNLi C H ~ 2 BuBr heptane THF 69-73% JACS (1970) 92 1396 A l k y l a t i o n o f a c i d s may a l s o be accomplished v i a e s t e r o r amide i n t e r m e d i a t e s . See s e c t i o n 113 ( E s t e r s f r o m E s t e r s ) and s e c t i o n 81 (Amides f r o m Amides) FOOH COOMe FOOH FHMe CMe CHMe p 2 FHMe y 2 FHMe I II 1 B r 2 P4 CH ___t CHMe 2 MeOH 3 Pyr KMn04 Me2CO FH2 I t fH2 FHMe CH2R CHMe I CH2R CH2R JCS (1963) 3081 PrCH2CH2COC1 1 Br2 2 i-PrCH20H 3 PhNEt2 PrCH=CHCOOCH2Pr-i KOH Biochem J (1951) CC13COOH SOCl2 __t DMF PrCOOH 300-340' 163 89% CC1 3COCl Helv (1959) 42 1653 Org S y n t h (1932) C o l l Vol 1 1 2 SECTION 1 7 C A R B O X Y L I C A C I D S , A C I D H A L I D E S AND A N H Y D R I D E S FROM C A R B O X Y L I C A C I D S AND A C I D H A L I D E S COOH 23 COCl JCS (1963) 491 98% JACS (1920) 42 599 Can J Chem (1955) 33 1515 t-BuCOOH PhCOCl t-BuCOC1 92% JACS (1938) PhCH2COOH PCl3 60 1325 PhCH2COC1 Org Synth (1943) C o l l Vol 2 156 - @‘O‘ H PBr3 Me $ODH Ph3P CCl4 acoBr 65% Me J C S (1934) 1406 FOC’ tHO CH20 JACS (1966) 3440 24 COMPENDIUM OF ORGANIC S Y N T H E T I C METHODS Annalen (1966) C 1 5 H 3 1 COOH N N ' - C a r b o n y 1 d i irni d a z o l e HC1 CHC13 * * MeCCl20Et 68% 694 78 PhCOCl Ber (1963) MeCH=CHCOOH 693 132 C15H31COCl Annalen (1966) PhCOOH SECTION 1 7 77% 96 1387 79% MeCH-CHCOC1 Rec Trav Chim (1957) 76 969 50-80% PhCOOH TsCl pyr ____t 97% (PhCO)20 JACS (1955) 77 6214 SECTION 17 CARBOXYLIC ACIDS, ACID HALIDES AND ANHYDRIDES FROM CARBOXYLIC ACIDS AND ACID HALIDES 25 60% JCS (1964) 755 J Lipid Res (1966) 1 1 7 4 Me[CH2],~H-~H[CH2I7COOH OH OH C1 COOEt Et3N THF (Me[CH,l,~H-~H[CH21,C0)20 OH OH JOC (1963) CTSH31COOH N-Trifluoroacetyl imidazole CgHg (C15H31C0)zO t Ber (1962) PhCOOAg 1905 cs2 95 54% 2073 ( PhCO)20 98% Proc Chem Soc (1957) 20 67% COMPENDIUM 26 PhCOOH 1 CH2=CO OF ORGANIC SYNTHETIC METHODS (PhCO)20 t 2 Distillation 96% 54 3427 JACS (1932) PrCOOH PhCOCH=CHCOPh Bu3P CgH6 ( PrCO) 2O * J O C (1964) Section 18 SECTION 18 77% 29 1385 Carboxylic Acids from Alcohols and Phenols 000000000000000000000000000000000000000000 Carboxylation o f alcohols .

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