Water → Methyl 2-(4-benzyloxyphenyl)acetate

HRID 523942Notes

Reaction equation

HRID 523942 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C(=O)C.COC(C)(C)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 2756645Methyl 2-(4-benzyloxyphenyl)acetate

Reagents, catalysts & solvents 2

HCID 15413tert-Butyl methyl etherSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

At room temperature, to a 3-L pear-shaped evaporating flask was added methyl(4-hydroxyphenyl)acetate (202 g) and potassium carbonate (233 g) which were dissolved in N,N-dimethylacetamide (DMA) (1 L). To the solution was added benzyl chloride (117 mL) at room temperature and stirred. The solution was then heated to 60° C. and stirred for 16 hours. The reaction solution was cooled to room temperature, diluted with methyl tert-butylether (MTBE) (1.3 L) and added with water (3 L) and an organic layer was extracted. The resulting organic layer was washed three times with a 1 N sodium hydroxide aqueous solution, then with water and a saturated sodium chloride solution and then dried over anhydrous magnesium sulphate. The solvent was distilled off at reduced pressure to give the titled compound (245 g) having the following physical properties.

Workup

  1. stirringstirred for 16 hours
  2. temperatureThe reaction solution was cooled to room temperature
  3. extractionan organic layer was extracted
  4. washThe resulting organic layer was washed three times with a 1 N sodium hydroxide aqueous solution
  5. dry with materialwith water and a saturated sodium chloride solution and then dried over anhydrous magnesium sulphate
  6. distillationThe solvent was distilled off at reduced pressure

Sources & evidence

ORD record
ord-d0b5f58d0a5a404885b9e725ca37c39e
Source dataset
uspto-grants-2016_05
Patent number
US09340499B2

Reaction notes

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