Potassium Carbonate → Biphenyl-4-carboxylic acid 2-methylbutyl ester

HRID 2073149Notes

Reaction equation

HRID 2073149 reaction equation
[CH3:1][CH:2]([CH2:20][CH3:21])[CH2:3][O:4][C:5]([C:7]1(O)[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH2:8]1)=[O:6].BrC(Br)CCCCCCCCCCC.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][CH:2]([CH2:20][CH3:21])[CH2:3][O:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 113249061,1-DibromododecaneHCID 678606924-Hydroxybiphenyl-4-carboxylic acid 2-methylbutyl ester

Product 1

HCID 19887231Biphenyl-4-carboxylic acid 2-methylbutyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

63 mmols (18 g) of the ester 1a obtained in Examples 1 and 2, 0.12 mol (39.4 g) of dibromododecane and 0.25 mol (34.6 g) of potassium carbonate were refluxed in 600 ml of acetone for 8 hours. The reaction mixture was filtered and the filtrate was concentrated, purified by column chromatography and recrystallized from ethanol to obtain 21.8 g (yield 65%) of 4'-12-bromodoecyloxy) biphenyl-4-carboxylic acid 2-methylbutyl ester {monobromo compound 1d, [α]23D=+2.85 (chloroform)}.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by column chromatography
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d35ffcf150c04635be09338706bf13e3
Source dataset
uspto-grants-1990_04
Patent number
US04915867

Reaction notes

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