Dichloromethane → Mesitol, alpha(sup 2),alpha(sup 6)-dichloro-

HRID 1868528Notes

Reaction equation

HRID 1868528 reaction equation
O[CH2:2][C:3]1[C:8]([OH:9])=[C:7](CO)[CH:6]=[C:5]([CH3:12])[CH:4]=1.O=S(Cl)[Cl:15].[CH2:17]([Cl:19])Cl>>[Cl:15][CH2:2][C:3]1[C:8]([OH:9])=[C:7]([CH2:17][Cl:19])[CH:6]=[C:5]([CH3:12])[CH:4]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 70392,6-Dimethylol-p-cresolHCID 24386Thionyl Chloride

Product 1

HCID 22146Mesitol, alpha(sup 2),alpha(sup 6)-dichloro-

Procedure

2,6-Bis(hydroxymethyl)-p-cresol (0.6779 g, 4.03 mmol) was suspended in CH2Cl2 (10 ml), and to this suspension was added slowly SOCl2 (3 ml, 41.1 mmol) under cooling in an ice-bath, and the resulting mixture was stirred at room temperature for 18 hours. The color of the reaction solution turned yellow. After completion of the reaction, the solvent was removed by evaporation to give 2,6-bis(chloromethyl)-p-cresol.

Workup

  1. temperatureunder cooling in an ice-bath
  2. customAfter completion of the reaction
  3. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-80d1497d8d804bc585bc7e76c5feae3e
Source dataset
uspto-grants-2009_12
Patent number
US07635776B2

Reaction notes

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