Triethylamine → 4-Methanesulfonyloxymethylbenzoic acid benzyl ester

HRID 2063328Notes

Reaction equation

HRID 2063328 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, methanesulfonyl chloride (2.1 mL, 27 mmol) was added to a solution of 4-hydroxymethylbenzoic acid benzyl ester (Reference Compound No. 7-1, 6.0 g, 24.8 mmol) and triethylamine (7.6 mL, 54 mmol) in dichloromethane (60 mL), and then the reaction mixture was stirred at room temperature for 50 minutes. Brine (0.30 L) was added to the reaction solution, and the mixture was extracted with chloroform (0.15 L) four times. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give 5.8 g of the title reference compound as yellow oil. (Yield 73%)

Workup

  1. extractionthe mixture was extracted with chloroform (0.15 L) 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 5.8 g of the title reference compound as yellow oil

Sources & evidence

ORD record
ord-6f262412d90e4b8b9762b713e54592a1
Source dataset
uspto-grants-2012_10
Patent number
US08288380B2

Reaction notes

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