4-Toluenesulfonyl chloride → (3-[4-(Toluene-4-sulfonyloxy)butyl]phenyl}acetic acid methyl ester

HRID 902623Notes

Reaction equation

HRID 902623 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:6]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1.O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14][O:15][S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=2)(=[O:25])=[O:24])[CH:6]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 59745064{3-[4-Hydroxybutyl]phenyl)acetic acid methyl ester

Product 1

HCID 86598282(3-[4-(Toluene-4-sulfonyloxy)butyl]phenyl}acetic acid methyl esterYield 63.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of {3-[4-hydroxybutyl]phenyl)acetic acid methyl ester (300 mg, 1.35 mmol) and p-toluenesulfonyl chloride (513 mg, 2.7 mmol) in pyridine (5 ml) was stirred at RT for 18 hr. The reaction was diluted with water (50 ml) and extracted with diethyl ether. The organic extracts were washed with water and cold 1N HCl, dried, and the solvent evaporated to give the title compound as an oil (322 mg, 63%). MS (ESI) 377.3 (M+H)+.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic extracts were washed with water and cold 1N HCl
  3. customdried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-ce9dc71d2f20480da1aa9df1808db461
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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