3-Chloro-1-propanol → 1-(3-Chloro-propoxymethyl)-2-methoxy-benzene

A solution of 24.6 g (0.157 mmol) of 2-methoxybenzyl chloride and 26 ml (29.4 g,0.311 mmol) of 3-chloro-1-propanol in 150 ml of absolute DMF was treated portionwise at 10° C. within 2.5 hours with 8.4 g (0.196 mmol) of sodium hydride dispersion (55% in refined oil) and stirred at room temperature for 1 hour. Subsequently, a further 1.0 g (0.023 mmol) of sodium hydride dispersion was added at room temperature and the mixture was stirred for a further 3 hours. For the working-up, the reaction mixture was partitioned between 500 ml of water and 500 ml of ethyl acetate. The organic phase was separated. The aqueous phase was extracted four times with 250 ml of ethyl acetate each time. The combined organic phases were washed twice with 250 ml of water each time and finally the solvent was distilled off under reduced pressure. The crude product (44 g) was purified by chromatography on silica gel with a 1:2 mixture of methylene chloride and hexane as the eluent. There were obtained 25.0 g (74% of theory) of 2-methoxybenzyl 3-chloropropyl ether as a colourless oil; MS: 214. 216 (M)+.

1. stirringthe mixture was stirred for a further 3 hours
2. customthe reaction mixture was partitioned between 500 ml of water and 500 ml of ethyl acetate
3. customThe organic phase was separated
4. extractionThe aqueous phase was extracted four times with 250 ml of ethyl acetate each time
5. washThe combined organic phases were washed twice with 250 ml of water each time
6. distillationfinally the solvent was distilled off under reduced pressure
7. customThe crude product (44 g) was purified by chromatography on silica gel with a 1:2 mixture of methylene chloride and hexane as the eluent

ORD record

ord-0d9484f38611461d807c502fd2381d56

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06150526