Methanol → Benzyl methyl ether

HRID 1607725Notes

Reaction equation

[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][OH:10]>>[CH3:9][O:10][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 887Methanol

HCID 7503Benzyl Chloride2×

Product 1

HCID 10869Benzyl methyl ether

Procedure

A solution of 10.5 gm(0.03 mol) of diamine 15, 4.0 gm(0.03 mol) of benzyl chloride, and 15 gm of MeOH were charged to the flask and heated to reflux. After 1.5 hours, GC showed 5-10% benzyl present along with amine. The reaction was allowed to reflux overnight(ca. 15 hr). GC showed the benzyl chloride consumed and some amine still present. Benzyl methyl ether was formed as a by-product of the reaction. Excess amine and other residue was removed by vigorous washing of the crude product in ether. After rotary evaporation, 10 gm(70% crude yield) of Quat 5 was obtained.

Workup

temperatureheated to reflux
temperatureto reflux overnight(ca. 15 hr)
customconsumed

Sources & evidence

ORD record: ord-aeab0864fcee4a459e2a2bb977f6c394
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04866192

Reaction notes

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