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

HRID 9867Notes

Reaction equation

HRID 9867 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

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 155390142-[(4-Dodecyloxyphenyl)sulfonyl]butanoic acid

Product 1

HCID 155390152-[(4-Dodecyloxyphenyl)sulfonyl]butanoyl Chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

2-[(4-Dodecyloxyphenyl)sulfonyl]butanoic acid (19.5 g, 47.33 mMole) was suspended in ethyl acetate (150 mL) to which was added several drops of dimethylformamide and thionyl chloride (14.4 mL, 119 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

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

Sources & evidence

ORD record
ord-bd37e20faae04c81914e2285bd65c7dd
Source dataset
uspto-grants-2006_08
Patent number
US07091361B2

Reaction notes

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