Methanol → 4-(2-Methoxyethyl)phenol

HRID 1450751Notes

Reaction equation

HRID 1450751 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[CH3:11]O>>[CH3:11][O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 10393Tyrosol

Product 1

HCID 925164-(2-Methoxyethyl)phenolYield 40%

Conditions

Temperature
100 °C

Procedure

A solution of twenty (20) grams 4-hydroxyphenethyl alcohol in 150 ml methanol containing 36.75 grams sulfuric acid (catalyst) were loaded into a 300 cc autoclave. The autoclave was then sealed and purged with nitrogen and pressurized with nitrogen gas to 500 psig. The autoclave was then heated to 100° C. with stirring at 300 rpm. The reaction was allowed to take place for approximately twenty-four (24) hours. The autoclave was then purged with nitrogen, cooled to 5° C., and vented slowly. The resultant material was 90 ml of a dark, greenish-black solution. An aliquot was treated with base and analyzed by gas chromatography (GC). A 40% yield of 4-(2'-methoxyethyl)phenol was obtained.

Workup

  1. customThe autoclave was then sealed
  2. custompurged with nitrogen
  3. customThe autoclave was then purged with nitrogen
  4. temperaturecooled to 5° C.
  5. additionAn aliquot was treated with base

Sources & evidence

ORD record
ord-7aebc78558d8449dba57076441235bdf
Source dataset
uspto-grants-1997_02
Patent number
US05602285

Reaction notes

Loading…