Water → Methyl 2-(4'-methanesulfonyloxymethylphenyl)benzoate

HRID 743759Notes

Reaction equation

HRID 743759 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>C(Cl)Cl>[CH3:26][S:27]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15380881Methyl 4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carboxylate

Product 1

HCID 15380882Methyl 2-(4'-methanesulfonyloxymethylphenyl)benzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10.0 g (41 mmol) of methyl 2-(4'-hydroxymethylphenyl)benzoate and 8.4 g (83.0 mmol) of triethylamine were dissolved in methylene chloride (150 ml). Under cooling with ice, a solution of 5.7 g (50 mmol) of methanesulfonyl chloride in methylene chloride (25 ml) was dropwise added thereto, followed by further stirring for one hour. The reaction liquid was poured into water, followed by the extraction with methylene chloride. After the organic phase was washed with water and dried, it was subjected to vacuum concentration. 13.1 g of the title compound was obtained as a wax (yield 100%). m.p.; 48°-45° C.

Workup

  1. temperatureUnder cooling with ice
  2. customThe reaction liquid
  3. extractionfollowed by the extraction with methylene chloride
  4. washAfter the organic phase was washed with water
  5. customdried
  6. concentrationit was subjected to vacuum concentration

Sources & evidence

ORD record
ord-2504ad0dae304cb5942a127f6d3d3ab0
Source dataset
uspto-grants-1996_09
Patent number
US05557002

Reaction notes

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