Methanol → 4-(2-Methoxyethyl)phenol

HRID 1450752Notes

Reaction equation

HRID 1450752 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 887Methanol2×HCID 10393Tyrosol

Product 1

HCID 925164-(2-Methoxyethyl)phenolYield 33%

Conditions

Temperature
150 °C

Procedure

A mixture of 80 grams of 4-hydroxyphenethyl alcohol (0.58 moles), methanol (100 ml), and 10 grams of Dowex 50 catalyst (H30 form, washed with methanol) was charged into a 300 cc autoclave. The autoclave was sealed, purged with nitrogen and then pressurized under nitrogen. The autoclave was heated to 150° C. overnight with stirring (about 16 hours). The reactor was then cooled, depressurized, and purged with nitrogen to remove by-product dimethyl ether. The catalyst was filtered off and a few drops of saturated aqueous sodium bicarbonate solution were added to neutralize acidity. The solvent was removed on a rotary evaporator. The product was isolated in 65% yield by distillation, with 33% of the 4-hydroxyphenethyl alcohol remaining unreacted.

Workup

  1. additionwas charged into a 300 cc autoclave
  2. customThe autoclave was sealed
  3. custompurged with nitrogen
  4. temperatureThe reactor was then cooled
  5. custompurged with nitrogen
  6. customto remove by-product dimethyl ether
  7. filtrationThe catalyst was filtered off
  8. additiona few drops of saturated aqueous sodium bicarbonate solution were added
  9. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-c8365fc556144990b21b9d225b7139e5
Source dataset
uspto-grants-1997_02
Patent number
US05602285

Reaction notes

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