Thionyl Chloride → Hexahydro-2,5-methano-pentalene-3a-carbonyl chloride

HRID 2198268Notes

Reaction equation

HRID 2198268 reaction equation
[CH2:1]1[CH:6]2[CH2:7][C:8]3([C:10]([OH:12])=O)[CH2:9][CH:2]1[CH2:3][CH:4]3[CH2:5]2.S(Cl)([Cl:15])=O>>[CH2:5]1[CH:4]2[C:8]3([C:10]([Cl:15])=[O:12])[CH2:9][CH:2]([CH2:1][CH:6]1[CH2:7]3)[CH2:3]2

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acid

Product 1

HCID 13182402Hexahydro-2,5-methano-pentalene-3a-carbonyl chloride

Procedure

A solution of 3-noradamantanecarboxylic acid (Aldrich, 4.5 g, 26 mmol) in 40 mL of thionyl chloride was warmed to reflux for 1 hour. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. The residue was dissolved in 40 mL benzene and concentrated under reduced pressure (3×) to afford hexahydro-2,5-methano-pentalene-3a-carbonyl chloride.

Workup

  1. temperatureto reflux for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 40 mL benzene
  4. concentrationconcentrated under reduced pressure (3×)

Sources & evidence

ORD record
ord-b450a8ae616840ddb7cf91649eb1cfdb
Source dataset
uspto-grants-2012_12
Patent number
US08338623B2

Reaction notes

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