Diethyl Ether → Methyl 2-[p-(benzyloxy)phenoxy]propionate

HRID 1164165Notes

Reaction equation

HRID 1164165 reaction equation
Br[CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[Na].[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCOCC>CN(C=O)C>[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:21][CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7638MonobenzoneHCID 95576Methyl 2-bromopropionateHCID 5360545Sodium

Product 1

HCID 13093988Methyl 2-[p-(benzyloxy)phenoxy]propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A 42 g (0.25 mole) portion of methyl 2-bromopropionate was added to 0.25 mole of the sodium salt of p-benzyloxyphenol (prepared from 13.5 g sodium methoxide and 50 g p-benzyloxyphenoxy) in 70 cc of DMF. The reaction mixture was heated at approximately 80° C. for 14.5 hours. The cooled reaction mixture was then poured into 1 liter ice-water. The product was isolated by ether extraction and was crystallized from methanol to give 45.2 g methyl 2-(4-benzyloxyphenoxy)propanoate, m.p. 38°-42°.

Workup

  1. customThe cooled reaction mixture
  2. customwas crystallized from methanol

Sources & evidence

ORD record
ord-645eb81ff1274448984f4dc6193efa2d
Source dataset
uspto-grants-1983_01
Patent number
US04368068

Reaction notes

Loading…