Methanol → 4'-(tert-Butyl)-[1,1'-biphenyl]-2-carboxylic acid

HRID 746985Notes

Reaction equation

HRID 746985 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5])C.CO.O.O.[OH-].[Li+]>C1COCC1>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:13][CH:14]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59711003Ethyl 4'-tert-butylbiphenyl-2-carboxylate

Product 1

HCID 136292864'-(tert-Butyl)-[1,1'-biphenyl]-2-carboxylic acidYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude 4′-tert-butylbiphenyl-2-carboxylic acid ethyl ester (33 g, ˜117 mmol) was taken up in a mixture of THF (100 mL), methanol (50 mL) and water (40 mL). Lithium hydroxide monohydrate (7.36 g, 176 mmol) was added and the reaction mixture was allowed to stir at room temperature for 3 days. The mixture was extracted three times with diethyl ether. The aqueous phase was then acidified using aq. 6N HCl and extracted three times with EtOAc. The combined EtOAc layers were dried over MgSO4, filtered and concentrated. The solid residue was triturated with hexane to afford the title compound as a white solid (18.7 g, 63%). 1H NMR (selected signals, DMSO-d6): 7.66 (dd, 1H), 7.53 (m, 1H), 7.41 (d, 2H), 7.25 (d, 2H), 1.29 (s 9H).

Workup

  1. extractionThe mixture was extracted three times with diethyl ether
  2. extractionextracted three times with EtOAc
  3. dry with materialThe combined EtOAc layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe solid residue was triturated with hexane

Sources & evidence

ORD record
ord-fae3a1b998004d1d99d0c4846a63b517
Source dataset
uspto-grants-2008_07
Patent number
US07393958B2

Reaction notes

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