Water → HCID 1729098, compound

HRID 2304057Notes

Reaction equation

HRID 2304057 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:12][S:13](Cl)(=[O:15])=[O:14].C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[CH3:12][S:13]([O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 4133Methyl SalicylateHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 1729098HCID 1729098, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl salicylate (200 g, 1310 mmoles) and methanesulfonyl chloride (210 g, 1830 mmoles) in toluene (600 ml), cooled at 5÷10° C. and under inert atmosphere (nitrogen), is slowly added (about 1 hour) with triethylamine (192 g, 1900 mmoles). The mixture is stirred for 20 hours, then poured into water (1500 ml) and the phases are separated. The aqueous phase is extracted twice with 250 ml of toluene. The combined organic phases are washed twice with 250 ml of water, dried over sodium sulfate, then evaporated under vacuum to a residue which is recrystallized from isopropanol (590 ml) to yield methyl 2-(methanesulfonyloxy)benzoate (280 g, 99.8% purity, 89% yield).

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is extracted twice with 250 ml of toluene
  3. washThe combined organic phases are washed twice with 250 ml of water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under vacuum to a residue which
  6. customis recrystallized from isopropanol (590 ml)

Sources & evidence

ORD record
ord-250f12d212c2445fa14b57371ab1832a
Source dataset
uspto-grants-2002_08
Patent number
US06433214B1

Reaction notes

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