Water → Ethyl 2-(3-(2-(3-hydroxyphenyl)2-oxoethyl)phenoxy)acetate

HRID 2073905Notes

Reaction equation

HRID 2073905 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:9])[CH2:10][C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=2)[O:17][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 147741341,2-Bis(3-hydroxyphenyl)ethanone

Product 1

HCID 14774136Ethyl 2-(3-(2-(3-hydroxyphenyl)2-oxoethyl)phenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,3'-dihydroxydeoxybenzoin (0.05 mol), ethyl bromoacetate (0.05 mol) ad K2CO3 (0.05 mol) in 50 mL of DMF is stirred at room temperature overnight. The reaction mixture is poured into water and extracted with EtOAc. The organic solution is dried and evaporated to dryness. The crude products are separtated by flash chromatography to give the ethyl 2-(3-(2-(3-hydroxyphenyl)-2-oxoethyl)phenoxy)acetate and the ethyl 2-(3-(2-(3-hydroxyphenyl)-1-oxoethyl)phenoxy)acetate.

Workup

  1. extractionextracted with EtOAc
  2. customThe organic solution is dried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-64e78115bf9d4228913b449b8c0205a9
Source dataset
uspto-grants-1990_04
Patent number
US04920131

Reaction notes

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