Propylene Oxide → 2-Propanol, 1-(3,5-dimethylphenoxy)-

HRID 1975544Notes

Reaction equation

[C:1]1([OH:9])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1.[CH2:10]1[O:13][CH:11]1[CH3:12].C(N(CC)CC)C>>[CH3:10][CH:11]([OH:13])[CH2:12][O:9][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[CH:2]=1

Participants

Reactant 3

HCID 6378Propylene Oxide

HCID 79483,5-Dimethylphenol

HCID 8471Triethylamine

Product 1

HCID 110739942-Propanol, 1-(3,5-dimethylphenoxy)-Yield 88.5%

Conditions

Temperature: 110 °C

Procedure

A 500 ml three-necked flask was charged with 51.88 g (425 mmol) of 3,5-xylenol, 29.6 g (510 mmol) of propylene oxide and 4.25 g (42 mmol) of triethylamine, and the resultant mixture was refluxed under heat at 90° C. for 1 hour and at 110° C. for 4 hours. The reaction product was recrystallized from hexane to give 1-methyl-2-(3,5-dimethylphenoxy)ethanol.

Workup

customThe reaction product was recrystallized from hexane

Sources & evidence

ORD record: ord-819adbdddbc04f5dad432e15c0210d8c
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05286905

Reaction notes

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