2-Naphthaleneacetic acid → 2-(2-Naphthyl)acetyl chloride

HRID 1731794Notes

Reaction equation

HRID 1731794 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([OH:14])=O.S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([Cl:17])=[O:14]

Participants

4

Reactant 2

HCID 113932-Naphthaleneacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 5881152-(2-Naphthyl)acetyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of β-naphthylacetic acid (25 g.) in chloroform (25 ml.) was added to a solution of thionyl chloride (50 ml.) in chloroform (80 ml.) and the mixture was heated under reflux for 1 hour, cooled and evaporated to dryness. The solid residue was crystallised from petroleum ether (b.p. 80°-100° C.) to give β-naphthylacetyl chloride, m.p. 67°-70° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. customevaporated to dryness
  5. customThe solid residue was crystallised from petroleum ether (b.p. 80°-100° C.)

Sources & evidence

ORD record
ord-628abf465d024022ba59d4b604de029f
Source dataset
uspto-grants-1986_11
Patent number
US04623660

Reaction notes

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