1-Adamantanecarboxylic acid → 1-Adamantanecarbonyl chloride

HRID 255118Notes

Reaction equation

HRID 255118 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-6ba041b10fc747589e2a4fab3c4f595a
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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