Hydrochloric Acid → [(4-Chlorobutoxy)methyl]benzene

HRID 1995571Notes

Reaction equation

HRID 1995571 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:16])=O.Cl.[Cl-].[Na+]>N1C=CC=CC=1>[Cl:16][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 24386Thionyl ChlorideHCID 5622124-Benzyloxy-1-butanol

Product 1

HCID 13521262[(4-Chlorobutoxy)methyl]benzeneYield 69.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A mixture of 4-benzyloxybutanol (64.8 g, 0.36 mol) in dry pyridine (200 ml) is stirred and heated to 50°-60° C. A solution of thionyl chloride (43 g, 0.36 mol) in pyridine (100 ml) is added slowly, and the mixture is kept at 60° C. for one more hour. After cooling to room temperature, the reaction mixture is poured into a mixture of ice and 2 N HCl. The mixture is saturated with sodium chloride, extracted with ether, and washed successively with water, 10% sodium bicarbonate, and water. Evaporation of solvent gives a yellow oil (49.7 g) which is distilled under vacuum to give the pure title compound (47 g), bp0.03-0.05 85°-90° C.

Workup

  1. temperatureheated to 50°-60° C
  2. customis kept at 60° C. for one more hour
  3. extractionextracted with ether
  4. washwashed successively with water, 10% sodium bicarbonate, and water
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-e941bbb6a7ca4851a4129df4c2b2400c
Source dataset
uspto-grants-1983_09
Patent number
US04405530

Reaction notes

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