Benzyl Chloride → 2,2-Dimethylpropanoic acid, 2,3,5-trimethyl-4-(phenylmethoxy)phenyl ester

HRID 374293Notes

Reaction equation

HRID 374293 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[C:3]([O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([OH:13])=[C:8]([CH3:14])[C:7]=1C)=[O:4].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:26](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:17][C:2]([CH3:1])([CH3:16])[C:3]([O:5][C:6]1[CH:7]=[C:8]([CH3:14])[C:9]([O:13][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:10]([CH3:26])[C:11]=1[CH3:12])=[O:4]

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 570114782,2-Dimethylpropanoic acid, 4-hydroxy-2,3,6-trimethylphenyl ester

Product 1

HCID 230757052,2-Dimethylpropanoic acid, 2,3,5-trimethyl-4-(phenylmethoxy)phenyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 43.5 g (184 mmol) of 2,2-dimethylpropanoic acid, 4-hydroxy-2,3,6-trimethylphenyl ester (Example A), 23.4 g (184 mmol) of benzyl chloride and 30.5 g (1.2×184 mmol) of anhydrous potassium carbonate in 500 mL of acetonitrile is stirred at reflux for 70 hours. The solid is removed and the reaction flask and solid are washed with fresh acetonitrile and the solvent removed on a rotary evaporator. The crude product amounts to 60.5 g which crystallizes on standing, mp 50°-53° C. Recrystallization from methanol in the presence of charcoal affords the title compound; mp 58°-59° C.

Workup

  1. temperatureat reflux for 70 hours
  2. customThe solid is removed
  3. washthe reaction flask and solid are washed with fresh acetonitrile
  4. customthe solvent removed on a rotary evaporator
  5. customcrystallizes
  6. customRecrystallization from methanol in the presence of charcoal

Sources & evidence

ORD record
ord-ca48aa99cef1470eb4d6526b44e65641
Source dataset
uspto-grants-1992_11
Patent number
US05166398

Reaction notes

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