Toluene → HCID 14317952, compound

HRID 1703404Notes

Reaction equation

HRID 1703404 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[C:13]1([OH:21])[C:14]([CH3:20])=[CH:15][CH:16]=[CH:17][C:18]=1[CH3:19].C1(C)C=CC=CC=1>O>[CH3:1][S:2]([O:21][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:20])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 113352,6-Dimethylphenol2×HCID 31297Methanesulfonyl chloride

Product 1

HCID 14317952HCID 14317952, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

12.5 Parts of methanesulphonyl chloride and 11.0 parts of triethylamine were added separately and simultaneously to a solution of 12.2 parts of 2,6-xylenol (the material available commercially from Synthetic Chemicals Limited and containing at least 92% 2,6-xylenol) in 65 parts of toluene over 40 minutes. The reaction mixture was mechanically agitated and the temperature was maintained at 40°-50° C. with external cooling. After agitating for a further 30 minutes, 24 parts of water were added, and the two phase mixture was separated. Evaporation of the organic phase gave 19.7 parts of 2,6-xylyl methanesulphonate. The product was purified by distillation at 188°-191° C. at 30 mm. On cooling the ester solidified, remelting at 26°-27° C.

Workup

  1. temperaturethe temperature was maintained at 40°-50° C. with external cooling
  2. stirringAfter agitating for a further 30 minutes
  3. customthe two phase mixture was separated
  4. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-b150df05f89e4222b0733403f47c9af1
Source dataset
uspto-grants-1982_09
Patent number
US04351968

Reaction notes

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