Water → 3,4-Dimethoxyphenethyl methanesulfonate

HRID 568781Notes

Reaction equation

HRID 568781 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[CH2:6][CH2:7][OH:8].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].O>C(Cl)Cl>[CH3:21][S:22]([O:8][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 819113,4-Dimethoxyphenethyl alcohol

Product 1

HCID 112076823,4-Dimethoxyphenethyl methanesulfonateYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 18.2 g (0.1 mole) of 3,4-dimethoxyphenethyl alcohol in 150 ml of methylene chloride was cooled to -5° C. To the solution was added 13.9 ml (0.1 mole) of triethylamine followed by 7.7 ml (0.1 mole) of methanesulfonyl chloride keeping the temperature below 0° C. The reaction was stirred for 4 hr, poured into water, washed with brine, dried over Na2SO4, and evaporated to give 26.7 g of product as a yellow oil.

Workup

  1. customthe temperature below 0° C
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-f14eb0cff26142d2a268cd9fa6fb201b
Source dataset
uspto-grants-1988_03
Patent number
US04729994

Reaction notes

Loading…