Triethylamine → 4-Methanesulfonyloxymethylbenzoic acid benzyl ester

HRID 658035Notes

Reaction equation

HRID 658035 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl.[Cl-].[Na+].O>[CH2:6]([O:13][C:14](=[O:23])[C:15]1[CH:16]=[CH:17][C:18]([CH2:21][O:22][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:19][CH:20]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15650225Benzyl 4-(hydroxymethyl)benzoate

Product 1

HCID 580012134-Methanesulfonyloxymethylbenzoic acid benzyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Under ice cooling, after methanesulfonyl chloride (2.1 mL, 27 mmol) was added to a solution of 4-hydroxymethylbenzoic acid benzyl ester (Reference Compound No. 6-1, 6.0 g, 25 mmol) and triethylamine (7.6 mL, 54 mmol) in dichloromethane (60 mL), the reaction mixture was stirred at room temperature for 50 minutes. Brine (300 mL) was added thereto, and then the whole was extracted with chloroform (150 mL) four times. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to give 1.8 g of the title reference compound as yellow oil. (Yield 73%)

Workup

  1. extractionthe whole was extracted with chloroform (150 mL) four times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customto give 1.8 g of the title reference compound as yellow oil

Sources & evidence

ORD record
ord-b1d69708bb2c449792ebb9a639ab9287
Source dataset
uspto-grants-2011_12
Patent number
US08076332B2

Reaction notes

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