Chloromethyl Methyl Ether → 3-Chloro-4-methoxymethoxy-5-methyl-1-benzoyloxybenzene

HRID 1387249Notes

Reaction equation

[C:1]([O:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([OH:17])=[C:12]([Cl:18])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][O:20][CH2:21]Cl.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl>[Cl:18][C:12]1[CH:11]=[C:10]([O:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:15]=[C:14]([CH3:16])[C:13]=1[O:17][CH2:19][O:20][CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Then, 25 g of 4-benzoyloxy-2-chloro-6-methylphenol was dissolved in 250 ml of chloroform, to which 12 g of chloromethyl methyl ether was added, while stirring at 0° C., and 21 g of N-ethyldiisopropylamine was added dropwise. After heating under reflux for 1 hour, the chloroform layer was washed with water, and concentrated. The residue was subjected to silica gel chromatography, which afforded 27.4 g of 3-chloro-4-methoxymethoxy-5-methyl-1-benzoyloxybenzene (96% yield).

Workup

additionwas added
temperatureAfter heating
temperatureunder reflux for 1 hour
washthe chloroform layer was washed with water
concentrationconcentrated

Sources & evidence

ORD record: ord-3aba41ebb34e40a88affb8866e842043
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268313B1

Reaction notes

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