Phenol → Methyl 2,2-dimethyl-3-phenoxypropanoate

HRID 1593244Notes

Reaction equation

HRID 1593244 reaction equation
[CH3:1][C:2]([CH3:19])([CH2:7]OS(C1C=CC(C)=CC=1)(=O)=O)[C:3]([O:5][CH3:6])=[O:4].[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>C(OCC)(=O)C.O>[CH3:1][C:2]([CH3:19])([CH2:7][O:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3]([O:5][CH3:6])=[O:4]

Participants

7

Reactant 4

HCID 996PhenolHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 22479327Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoate

Product 1

HCID 22479306Methyl 2,2-dimethyl-3-phenoxypropanoateYield 414%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2,2-dimethyl-3-(4-toluenesulfonyloxy)propionate (Intermediate A35, 80 g, 0.28 mol), phenol (28 g, 0.029 mol), potassium carbonate (58 g, 0.42 mol), and 250 mL N,N-dimethylacetamide was stirred and heated at reflux for 4 hr. The reaction mixture was cooled, diluted with ethyl acetate, and poured into water. The organic phase was washed with water and concentrated under reduced pressure. The residue was dissolved in hexanes and washed with water, 1 M sodium hydroxide, and a second portion of water. The concentrated solution was distilled at 15 torr (34-37° C.) to yield 25 g (42%) of the methyl 2,2-dimethyl-3-phenoxypropionate.

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hr
  3. temperatureThe reaction mixture was cooled
  4. washThe organic phase was washed with water
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in hexanes
  7. washwashed with water, 1 M sodium hydroxide
  8. distillationThe concentrated solution was distilled at 15 torr (34-37° C.)

Sources & evidence

ORD record
ord-6d80325affcd4a2dac37221ff3b276cf
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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