Potassium Carbonate → 5-[3,5-Dimethyl-4-(phenylmethoxy)phenoxy]-2,2-dimethylpentanoic acid, methyl ester

HRID 374287Notes

Reaction equation

HRID 374287 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[C:6]([CH3:16])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br[CH2:19][CH2:20][CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:16][C:6]1[CH:5]=[C:4]([CH:3]=[C:2]([CH3:1])[C:7]=1[O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[O:17][CH2:19][CH2:20][CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13050502Methyl 5-bromo-2,2-dimethylpentanoateHCID 226253934-(Benzyloxy)-3,5-dimethylphenol

Product 1

HCID 867463865-[3,5-Dimethyl-4-(phenylmethoxy)phenoxy]-2,2-dimethylpentanoic acid, methyl esterYield 112.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 11.3 g (49.6 mmol) of 3,5-dimethyl-4-(phenylmethoxy)phenol (Example G), 13.3 g (1.2×49.6 mmol) of 5-bromo-2,2-dimethylvaleric acid, methyl ester (U.S. Pat. No. 4,665,226) and 8.2 g (1.2×49.6 mmol) of anhydrous potassium carbonate in 300 mL of acetonitrile is stirred at reflux for 18 hours. The reaction flask and inorganic residue are washed with fresh acetonitrile and the solvent is removed. A diethyl ether solution of the residual product is washed with 50 mL of 2N potassium hydroxide solution, brine, dried and evaporated leaving 20.6 g of the product as a pale yellow oil. Distillation through a short path apparatus affords 15.4 g of the title compound; bp 190°-194° C./0.1 mm (230°-240° C).

Workup

  1. temperatureat reflux for 18 hours
  2. washThe reaction flask and inorganic residue are washed with fresh acetonitrile
  3. customthe solvent is removed
  4. washA diethyl ether solution of the residual product is washed with 50 mL of 2N potassium hydroxide solution, brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-0863481a84ae47ae850818fc29500e7d
Source dataset
uspto-grants-1992_11
Patent number
US05166398

Reaction notes

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