4-Toluenesulfonyl chloride → HCID 22492958, compound

HRID 1816344Notes

Reaction equation

HRID 1816344 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:21][C:11]1[CH:16]=[CH:15][C:14]([S:17]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:19])=[O:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 154095297-Methoxy-1-heptanol

Product 1

HCID 22492958HCID 22492958, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 7-methoxy-1-heptanol (18.1 g) and p-toluenesulfonyl chloride (28.4 g) in dichloromethane (180 ml) was added triethylamine. After stirring for 27.5 hours at room temperature, the solvent was evaporated in vacuo. Then the residue was poured into a mixture of ethyl acetate and water. The organic layer was successively washed with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (8:1→5:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 7-methoxyheptyl 4-methylbenzenesulfonate (28.5 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. additionThen the residue was poured into a mixture of ethyl acetate and water
  3. washThe organic layer was successively washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (8:1→5:1)
  7. additionThe eluted fractions containing the desired product
  8. customwere collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-476f520840ee498a9003e79beb4b4f35
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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