Ethyl bromoacetate → Ethyl 2-[4-(2-hydroxyethyl)phenoxy]acetate

HRID 843314Notes

Reaction equation

HRID 843314 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 11775791Ethyl 2-[4-(2-hydroxyethyl)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-(2-hydroxyethyl)phenol (5 g) in acetone (45 mL) was added anhydrous potassium carbonate (6.5 g) at room temperature, and the mixture was stirred for 30 minutes. Ethyl bromoacetate (4.4 mL) was added dropwise to the reaction mixture at 40-45° C. of internal temperature, and the mixture was stirred at 40° C. for 8 hours. After the insoluble materials were filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate) to give ethyl 2-[4-(2-hydroxyethyl)phenoxy]acetate (5.8 g).

Workup

  1. stirringthe mixture was stirred at 40° C. for 8 hours
  2. filtrationAfter the insoluble materials were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1f7d5ba735b04542a5b0343b3e1316bf
Source dataset
uspto-grants-2002_04
Patent number
US06376707B1

Reaction notes

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