Thionyl Chloride → 2-(Bicyclo(2.2.1)heptan-2-yl)acetyl chloride

HRID 1853402Notes

Reaction equation

HRID 1853402 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([OH:11])=O.S(Cl)([Cl:14])=O>>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][C:9]([Cl:14])=[O:11]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 79139Norborn-2-ylacetic acid

Product 1

HCID 146225842-(Bicyclo(2.2.1)heptan-2-yl)acetyl chlorideYield 100%

Procedure

2-Norbornaneacetic acid (Aldrich, Catalog #127264, CAS #1007-01-8, 2.01 g, 13.0 mmol) was dissolved in thionyl chloride (7 mL, 96 mmol). The reaction was heated to reflux for 5 hours. The reaction mixture was concentrated in vacuo to provide the title compound as a colorless oil (2.24 g, 100%) that was used without additional purification.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-d7b810ee65a74c0388db91dc0ac55f10
Source dataset
uspto-grants-2015_02
Patent number
US08962639B2

Reaction notes

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