Thionyl Chloride → 1-Phenylcyclopentane-1-carbonyl chloride

HRID 987373

Reaction equation

HRID 987373 reaction equation
[C:1]1([C:7]2([C:12]([OH:14])=O)[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:17])=O>>[C:1]1([C:7]2([C:12]([Cl:17])=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 661671-Phenylcyclopentanecarboxylic acid

Product 1

HCID 123789051-Phenylcyclopentane-1-carbonyl chloride

Procedure

The carboxylic acid chlorides used in the synthesis of the parent amides were all synthesized as described below. In a 1-liter 3-neck flask, 200 gm (1.05 mole) of 1-phenylcyclopentanecarboxylic acid (ACROS ORGANICS) was added drop-wise to stirring excess of thionyl chloride (Aldrich) under nitrogen. The resulting mixture was heated at reflux for two hrs. The reaction was further stirred at room temperature overnight. The resulting brown-red solution was concentrated at reduced pressure and heat on a rotary evaporator to remove excess thionyl chloride. The reaction yielded 216 gm of a lachrymator substance whose 1H-NMR and 13C-NMR spectra were ideal for the desired acid chloride.

Workup

  1. customall synthesized
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for two hrs
  4. concentrationThe resulting brown-red solution was concentrated at reduced pressure
  5. temperatureheat on a rotary evaporator
  6. customto remove excess thionyl chloride
  7. customThe reaction yielded 216 gm of a lachrymator substance whose 1H-NMR

Sources & evidence

ORD record
ord-36941de0738b4097846b493508455e7e
Source dataset
uspto-grants-2003_10
Patent number
US06632417B2

Linked notes

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