Acetic Acid → 4'-(12-Acetyloxydodecyloxy)biphenyl-4-carboxylic acid ethyl ester

HRID 2082125Notes

Reaction equation

HRID 2082125 reaction equation
O.O.O.O.O.[OH-].C[N+](C)(C)C.CN(C=O)C.[C:17]([OH:20])(=[O:19])[CH3:18].[CH2:21]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]Br)=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=[O:25])[CH3:22]>CCOCC>[CH2:21]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][O:20][C:17](=[O:19])[CH3:18])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=[O:25])[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 82620Tetramethylammonium Hydroxide PentahydrateHCID 539084014'-(12-Bromododecyloxy)biphenyl-4-carboxylic acid ethyl ester

Product 1

HCID 536569284'-(12-Acetyloxydodecyloxy)biphenyl-4-carboxylic acid ethyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

60 m moles (10.9 g) of tetramethylammonium hydroxide pentahydrate was added to a DMF solution of 60 m moles (3.6 g) of acetic acid, and stirred for one hour, then 50 m moles (24.5 g) of the above 4'-(12-bromododecyloxy)biphenyl-4-carboxylic acid ethyl ester was added thereto, and stirred for 12 hours. After the reaction, the reaction solution was ether extracted. The extrate was concentrated, and then purified by column chromatography, to obtain 15.7 g of 4'-(12-acetyloxydodecyloxy)biphenyl-4-carboxylic acid ethyl ester [m.p. 80.1°-81.5° C⟧ (yield: 67%)

Workup

  1. stirringstirred for 12 hours
  2. customAfter the reaction
  3. extractionextracted
  4. concentrationThe extrate was concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-14a366defe6c471fb19cebf32448c604
Source dataset
uspto-grants-1993_02
Patent number
US05187248

Reaction notes

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