3-Chloro-1-propanol → 3-(3-chlorophenoxy)propan-1-ol
Reaction equation
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Cl[CH2:11][CH2:12][CH2:13][OH:14]>>[Cl:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:11][CH2:12][CH2:13][OH:14]Participants
Procedure
To a solution of 37.3 g. (0.2 mol) 3-(3-chlorophenoxy)-1-propanol (obtained by the reaction of 3-chlorophenol sodium salt with 3-chloro-1-propanol in boiling ethanol; b.p.0.4 =112°-116°; yield 84%) and 42 ml. (0.3 mol) triethylamine in 150 ml. chloroform, one adds dropwise, with stirring, exclusion of moisture and cooling to -15°, a solution of 20 ml. (0.26 mol) methanesulphonic acid chloride in 50 ml. chloroform within 2 hrs., stirs for a further 2 hrs. at -10°, leaves to come to room temperature overnight and pours the reaction mixture, with stirring, into a mixture of 300 ml. ice water and 5 ml. 36% hydrochloric acid. After separating off the chloroform phase, one washes it twice with 100 ml. amounts of water and subsequently with aqueous sodium hydrogen carbonate solution to remove acid, dries over anhydrous sodium sulphate and evaporates under reduced pressure. One obtains, in practically quantitative yield (58.7 g.) 3-(3-chlorophenoxy)-propyl 1-methanesulphonate, still containing about 10% chloroform, as a slowly crystallising oil. The crystallisate has, after washing with petroleum ether and drying in a vacuum desiccator, the m.p. 36°-37°.
Sources & evidence
- ORD record
- ord-7b29396b6f2f43248d7e911cec2e2995
- Source dataset
- uspto-grants-1982_12
- Patent number
- US04363805
Reaction notes
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