Sodium Hydroxide → 4-[1-(4-Bromo-3-[1,3]dioxan-2-yl-phenoxy)-3-methyl-butyl]-benzoic acid

HRID 1914329Notes

Reaction equation

HRID 1914329 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([O:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[C:18]([CH:23]3[O:28][CH2:27][CH2:26][CH2:25][O:24]3)[CH:17]=2)[CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[CH:5][CH:6]=2)[CH2:11][CH:12]([CH3:13])[CH3:14])=[CH:17][C:18]=1[CH:23]1[O:24][CH2:25][CH2:26][CH2:27][O:28]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671533784-[1-(4-Bromo-3-[1,3]dioxan-2-yl-phenoxy)-3-methyl-butyl]-benzoic acid methyl ester

Product 1

HCID 671534564-[1-(4-Bromo-3-[1,3]dioxan-2-yl-phenoxy)-3-methyl-butyl]-benzoic acidYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of 4-[1-(4-bromo-3-[1,3]dioxan-2-yl-phenoxy)-3-methyl-butyl]-benzoic acid methyl ester (1000 mg) in methanol (20 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 (940 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-8a1c1bb0d21241fa9ab53a45faa5fdbe
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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