Potassium Carbonate → Methyl (4-hydroxymethyl-2-propylphenoxy)-2-phenylacetate

HRID 1645956Notes

Reaction equation

HRID 1645956 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12].Br[CH:14]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([O:17][CH3:18])=[O:16])=[C:3]([CH2:10][CH2:11][CH3:12])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 220112094-(Hydroxymethyl)-2-propylphenol

Product 1

HCID 19802778Methyl (4-hydroxymethyl-2-propylphenoxy)-2-phenylacetateYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 0.484 g (2.91 mmol) of the product of Step F dissolved in 12 mL of acetone were added 0.667 g (2.91 mmol) of methyl 2-bromo-2-phenylacetate, 0.804 g (5.82 mmol) of anhydrous K2CO3 and the mixture was stirred and heated at reflux for 5 hours. The mixture was then cooled, filtered and evaporated in vacuo. The residual oil was purified on a silica gel flash chromatography column eluted with 30% ethyl acetate/hexane to afford 0.756 g (83%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residual oil was purified on a silica gel flash chromatography column
  7. washeluted with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7a00f74df82849c49c88a111d3c747f4
Source dataset
uspto-grants-1993_01
Patent number
US05177095

Reaction notes

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