Triethylamine → HCID 21704982, compound

HRID 1595539Notes

Reaction equation

HRID 1595539 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([OH:17])[CH2:7][C:8]1[CH:16]=[CH:15][C:13]([OH:14])=[C:10]([O:11][CH3:12])[CH:9]=1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:17][CH2:6][CH2:7][C:8]1[CH:16]=[CH:15][C:13]([O:14][S:2]([CH3:1])(=[O:4])=[O:3])=[C:10]([O:11][CH3:12])[CH:9]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16928Homovanillyl alcoholHCID 31297Methanesulfonyl chloride

Product 1

HCID 21704982HCID 21704982, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

44 g (0.39 mole) methanesulfonyl chloride was slowly added to a solution of 30 g (0.178 mole) homovanillyl alcohol and 45.3 g (0.45 mmole) triethylamine in 500 ml dichloromethane at −10° C. After stirring at room temperature over night the salts were filtered off, the organic phase was washed with sodium bicarbonate and brine, dried (magnesium sulfate) and evaporated in vacuo to give 50 g (yield 86%) of 3-methoxy-4-(methylsulfonyloxy)phenethyl methanesulfonate.

Workup

  1. filtrationwere filtered off
  2. washthe organic phase was washed with sodium bicarbonate and brine
  3. dry with materialdried (magnesium sulfate)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-af6a52593a144d86b67a51def093643b
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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