Methanesulfonyl chloride → 2-(3-Chloropropyl)-6-methylphenol

HRID 343485Notes

Reaction equation

HRID 343485 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12].CS([Cl:17])(=O)=O>CO>[Cl:17][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 543527972-(3-Hydroxypropyl)-6-methylphenol

Product 1

HCID 544438172-(3-Chloropropyl)-6-methylphenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
110 °C

Procedure

A solution of N,N-dimethylaniline (24.0 mL) in toluene (20.0 mL) was bubbled with hydrochloride gas to prepare the corresponding hydrochloride. To the mixture were added 2-(3-hydroxypropyl)-6-methylphenol (20.0 g) and methanesulfonyl chloride (10.2 mL), and the resulting mixture was stirred at 110° C. for 1.5 hours. After cooling, methanol (2.4 mL) was added to the reaction mixture. The mixture was washed with distilled water, an aqueous sodium bicarbonate solution, distilled water and brine successively and then evaporated to give a solution of 2-(3-chloropropyl)-6-methylphenol (19.9 g) in toluene (21 g). NMR spectrum of this compound was identical with that of Reference Example 12.

Workup

  1. customA solution of N,N-dimethylaniline (24.0 mL) in toluene (20.0 mL) was bubbled with hydrochloride gas
  2. customto prepare the corresponding hydrochloride
  3. temperatureAfter cooling
  4. washThe mixture was washed with distilled water
  5. distillationan aqueous sodium bicarbonate solution, distilled water and brine successively
  6. customevaporated

Sources & evidence

ORD record
ord-7179a961a0084adea8521b87d4c07711
Source dataset
uspto-grants-1999_01
Patent number
US05861437

Reaction notes

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