3-Hydroxybenzyl alcohol → 3-(Chloromethyl)phenol

HRID 17873

Reaction equation

HRID 17873 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]O.C(N(CC)CC)C.S(Cl)([Cl:19])=O>C1C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][Cl:19]

Participants

5

Procedure

3-Hydroxybenzylalcohol (5 g, 40 mmol) and triethylamine (5.2 ml, 60 mmol) were dissolved in benzene (250 ml), and thionylchloride (5.2 ml) dissolved in benzene (50 ml) was added thereto at 0° C. The brownish reacting solution was stirred at room temperature for 6 hours. When the reaction was completed, the solution was washed with brine, and the water layer was extracted with methylene chloride. The organic extract was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure to obtain the title compound (5.7 g, 99%).

Workup

  1. additionwas added
  2. customat 0° C
  3. washthe solution was washed with brine
  4. extractionthe water layer was extracted with methylene chloride
  5. extractionThe organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-1d9b2f92f1e840efb716f8ecf6ea906d
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Linked notes

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