Water → HCID 86642396, compound

HRID 1361093Notes

Reaction equation

HRID 1361093 reaction equation
[CH2:1]([S:5](Cl)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].[C:9]1([O:19][CH3:20])[C:10](=[CH:12][CH:13]=[C:14]([CH:18]=1)[CH2:15][CH:16]=[CH2:17])[OH:11].C(N(CC)CC)C.O>ClCCl>[CH2:1]([S:5]([O:11][C:10]1[CH:12]=[CH:13][C:14]([CH2:15][CH:16]=[CH2:17])=[CH:18][C:9]=1[O:19][CH3:20])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 3314EugenolHCID 8471TriethylamineHCID 754301-Butanesulfonyl chloride

Product 1

HCID 86642396HCID 86642396, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

13 ml (0.1 mol) of butanesulfonyl chloride are added dropwise to a solution of 15 g (0.09 mol) of eugenol and 16 ml (0.11 mol) of triethylamine in 150 ml of dichloromethane cooled beforehand to −20° C. The reaction mixture is stirred for 4 hours at room temperature. The reaction is treated by adding 50 ml of water and extracting with dichloromethane. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue is purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 24.3 g (74%) of 4-allyl-2-methoxyphenyl 1-butane-1-sulfonate are obtained in the form of a yellow oil.

Workup

  1. additionThe reaction is treated
  2. extractionextracting with dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by chromatography on a column of silica
  7. washeluted with a 90/10 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-0cb7beea4179474f99ddbbeea931df03
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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