Phenol → Methyl 2-hydroxy-3-phenoxy-3,3-diphenylpropionate

HRID 251401Notes

Reaction equation

HRID 251401 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:13][CH:8]2[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]1([OH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[OH:13][CH:8]([C:7]([O:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

3

Reactant 2

HCID 996PhenolHCID 10587027Methyl 3,3-diphenyloxirane-2-carboxylate

Product 1

HCID 10521673Methyl 2-hydroxy-3-phenoxy-3,3-diphenylpropionateYield 77%

Procedure

5 g (19.6 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate and 5.6 g (60 mmol) of phenol were heated together at 100° C. for 6 h. Removal of the excess phenol by distillation under high vacuum and purification of the residue by chromatography on silica gel with hexane/ethyl acetate mixtures resulted in 4.9 g (77%) of a pale yellow oil.

Workup

  1. customRemoval of the excess phenol
  2. distillationby distillation
  3. customunder high vacuum and purification of the residue by chromatography on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-0f6a920f42df4b7c98e22e917ca0c41f
Source dataset
uspto-grants-2011_01
Patent number
US07863445B2

Reaction notes

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