Triethylamine → 4-(Methylcarbonyloxy)phenethyl methanesulfonate

HRID 1595512

Reaction equation

HRID 1595512 reaction equation
[CH3:1][C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1)=[O:3].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([O:13][CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([CH3:1])=[O:3])=[CH:6][CH:7]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 586676Benzeneethanol, 4-(acetyloxy)-

Product 1

HCID 217049894-(Methylcarbonyloxy)phenethyl methanesulfonateYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

55 g (0.305 mole) 2-(4-methylcarbonyloxyphenyl)-1-ethanol and 34.4 g (0.341 mole) triethylamine in 300 ml dichloromethane were cooled on an ice bath. 38.5 g (0.336 mole) methanesulfonyl chloride was slowly added. The ice bath was removed and the mixture was stirred for 3 hours at room temperature. Water was added and the phases were separated. The organic phase was washed with saturated sodium hydrogen bicarbonate and brine, dried (magnesium sulfate), filtered and evaporated in vacuo to give 76.6 g (yield 97%) of 4-(methylcarbonyloxy)phenethyl methanesulfonate.

Workup

  1. customThe ice bath was removed
  2. additionWater was added
  3. customthe phases were separated
  4. washThe organic phase was washed with saturated sodium hydrogen bicarbonate and brine
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ebd58084eae847f7b137bb1746131eae
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Linked notes

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