Sodium Hydroxide → 4-[1-(4'-Isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoic acid

HRID 1160928Notes

Reaction equation

HRID 1160928 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:14][C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([C:22]3[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][CH:23]=3)=[C:17]([CH3:31])[CH:16]=2)[CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[CH:28]([C:25]1[CH:24]=[CH:23][C:22]([C:18]2[C:19]([CH3:21])=[CH:20][C:15]([O:14][CH:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:32])=[O:2])=[CH:5][CH:6]=3)[CH:11]([CH3:13])[CH3:12])=[CH:16][C:17]=2[CH3:31])=[CH:27][CH:26]=1)([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671535504-[1-(4'-Isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoic acid methyl ester

Product 1

HCID 671535774-[1-(4'-Isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoic acidYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of isomer 1 of 4-[1-(4′-isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoic acid methyl ester (510 mg) in methanol (10 mL) is added sodium hydroxide (5 N aqueous, 2 mL) and stirred for 4 h. The reaction mixture is concentrated and acidified by 5 N HCl (2 mL), extracted with ethyl acetate. Combined organic layers are washed with water and brine, dried over sodium sulfate. Concentration gives the title compound (450 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted with ethyl acetate
  3. washCombined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-f980f747b4d94962b1158431822a1914
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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