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

HRID 1914342Notes

Reaction equation

HRID 1914342 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-858f35d108a849ceb36fce169cae70ac
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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