Ethylene carbonate → 2-(5-Fluoro-2-methoxyphenoxy)ethanol

HRID 1073851Notes

Reaction equation

HRID 1073851 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.C1(=O)O[CH2:14][CH2:13][O:12]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([CH:7]=1)[O:8][CH2:14][CH2:13][OH:12]

Participants

6

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 27745595-fluoro-2-methoxyphenol

Product 1

HCID 150799632-(5-Fluoro-2-methoxyphenoxy)ethanolYield 79.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

A suspension of 8.75 g of 5-fluoro-2-methoxyphenol, 10.9 g of ethylene carbonate and 8.50 g of potassium carbonate in 12 ml of toluene was refluxed for 2.5 hours. The reaction mixture was diluted with benzene, washed with water, dried and evaporated. The residue was distilled to give 9.15 g of 2-(5-fluoro-2-methoxyphenoxy)ethanol as colorless oil, b.p. 138°-140° C. (8mmHg).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. distillationThe residue was distilled

Sources & evidence

ORD record
ord-b9a9945b2083473f800340acad563587
Source dataset
uspto-grants-1990_11
Patent number
US04971990

Reaction notes

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