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

HRID 1082020
Notes
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Reaction equation

HRID 1082020 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent
2×

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%).

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-f040c74a4b8c4f5b8591d7e0b1e9c9dd
Source dataset
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05587504

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes