Sulfuryl chloride → HCID 19348427, compound

HRID 1418215Notes

Reaction equation

S(Cl)([Cl:4])(=O)=O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:9]([O:24][CH3:25])[CH:8]=1>C1C=CC=CC=1.C(OCC)(=O)C>[Cl:4][C:12]1[C:7]([OH:6])=[CH:8][C:9]([O:24][CH3:25])=[C:10]([CH:13]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:11]=1

Participants

Conditions

Temperature: 70 °C

Procedure

604 mg (4.48 mmol) of sulfuryl chloride were added to a solution of 1.26 g (4.48 mmol) of methyl 3-(4-hydroxy-2-methoxyphenyl)octanoate (prepared as described in Preparation 44) in 10 ml of benzene, and the resulting mixture was stirred at 70° C. for 3.5 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate, and the diluted solution was washed with an aqueous solution of sodium carbonate, with water and with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 100 g of silica gel, using a 1:2 by volume mixture of ethyl acetate and hexane as the eluent, to give the title compound as an oily substance in a 88% yield.

Workup

washthe diluted solution was washed with an aqueous solution of sodium carbonate, with water and with a saturated aqueous solution of sodium chloride
dry with materialafter which it was dried over anhydrous magnesium sulfate
customThe solvent was then removed by distillation under reduced pressure
customthe resulting residue was purified by column chromatography through 100 g of silica gel
additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record: ord-0a4c04d285e54986941c85a3c3da575e
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05880147

Reaction notes

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