1-Adamantanecarboxylic acid → 1-Adamantanecarbonyl chloride

HRID 1470006Notes

Reaction equation

HRID 1470006 reaction equation
[C:1]12([C:11]([OH:13])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.S(Cl)([Cl:16])=O>>[C:1]12([C:11]([Cl:16])=[O:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

3

Reactant 2

HCID 132351-Adamantanecarboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 989151-Adamantanecarbonyl chloride

Procedure

A solution of 1-adamantanecarboxylic acid (0.27 g, 1.5 mmol) in 5 mL of thionyl chloride was warmed to reflux and stirred for 2 hours. The mixture was cooled to ambient temperature and concentrated under reduced pressure. The residue was diluted with 5 mL of toluene and concentrated under reduced pressure three times to afford the title compound, which was used without additional purification or characterization.

Workup

  1. temperatureto reflux
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with 5 mL of toluene
  4. concentrationconcentrated under reduced pressure three times

Sources & evidence

ORD record
ord-493b14be47b54e7eb4326bb270145969
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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