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

HRID 231016

Reaction equation

HRID 231016 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-5d549c02b7d2406ca2f303f466140caa
Source dataset
uspto-grants-1989_07
Patent number
US04844835

Linked notes

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