Water → 4-Propylbenzyl methanesulfonate

HRID 1888707Notes

Reaction equation

HRID 1888707 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>C1COCC1>[CH3:19][S:20]([O:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=1)(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2760472(4-Propylphenyl)methanol

Product 1

HCID 580472854-Propylbenzyl methanesulfonateYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-propylphenyl)methanol (116 mg, 0.770 mmol) in THF (5 mL) were added triethylamine (0.220 mL, 1.54 mmol) and methanesulfonyl chloride (89.0 mL, 1.16 mmol), and the mixture was stirred at room temperature for 15 min. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (176 mg, quantitative). This was used for the next step without purification.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-90f0223593d144df8099ca67a6ac8fd0
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

Loading…