3,4-Dichloroaniline → trans-2-(3,4-Dichloroanilino)cyclopentanol

HRID 1856005Notes

Reaction equation

HRID 1856005 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].[CH:10]12[O:15][CH:11]1[CH2:12][CH2:13][CH2:14]2>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH:5][C@@H:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[OH:15]

Participants

3

Reactant 2

HCID 72573,4-DichloroanilineHCID 92446-Oxabicyclo[3.1.0]hexane

Product 1

HCID 12862635trans-2-(3,4-Dichloroanilino)cyclopentanolYield 44%

Procedure

A solution of 50.0 g. (0.31 mole) of 3,4-dichloroaniline in100 ml. of cyclopentene oxide is refluxed for 7 days. The solution is evaporated and the residue triturated with 250 ml. of petroleum ether (b.p. 30°-60° C.) five times to remove unreacted 3,4-dichloroaniline. The residue is treated with excess ethereal hydrogen chloride and the resulting crude hydrochloride salt is recrystallized twice from a methanol/ethyl ether mixture to give trans-2-(3,4-dichloroanilino)cyclopentanol, 38.7 g. (44% yield), m.p. 167°-168° C. The ultraviolet, infrared and nuclear magnetic resonance spectra are consistent with the structure of this product.

Workup

  1. customThe solution is evaporated
  2. customthe residue triturated with 250 ml
  3. customof petroleum ether (b.p. 30°-60° C.) five times to remove unreacted 3,4-dichloroaniline
  4. additionThe residue is treated with excess ethereal hydrogen chloride
  5. customthe resulting crude hydrochloride salt is recrystallized twice from a methanol/ethyl ether mixture

Sources & evidence

ORD record
ord-3def6422265b4a018b865d2a32133c1f
Source dataset
uspto-grants-1980_08
Patent number
US04217362

Reaction notes

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