Thionyl Chloride → 2-[(4-Dodecyloxyphenyl)sulfonyl]butanoyl Chloride

HRID 9871Notes

Reaction equation

[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH:23]([CH2:27][CH3:28])[C:24](O)=[O:25])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].S(Cl)([Cl:31])=O>C(OCC)(=O)C.CN(C)C=O>[CH2:1]([O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH:23]([CH2:27][CH3:28])[C:24]([Cl:31])=[O:25])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: 70 °C

Procedure

2-[(4-Dodecyloxyphenyl)sulfonyl]butanoic acid (1.1 g, 26.92 mMole) was suspended in ethyl acetate (100 mL) to which was added several drops of dimethylformamide and thionyl chloride (10.0 mL, 134.6 mMole). The mixture was heated at 70° C. for 1.5 hours, cooled, concentrated under reduced pressure, co-evaporated with ethyl acetate (2×100 mL) and the oil so obtained used as such in the next step of the reaction sequence.

Workup

temperaturecooled
concentrationconcentrated under reduced pressure, co-evaporated with ethyl acetate (2×100 mL)
customthe oil so obtained

Sources & evidence

ORD record: ord-8a5d47f9ffdd4f8e93a6b58ac33ac070
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091361B2

Reaction notes

Loading…