Isopropanol → 4-(3,4-Dichlorophenyl)-2-oxazolone

HRID 395673

Reaction equation

HRID 395673 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=O.[C-]#[N:14].[K+].C[CH:17]([OH:19])C>C(O)(=O)C>[Cl:12][C:7]1[CH:6]=[C:5]([C:3]2[NH:14][C:17](=[O:19])[O:1][CH:2]=2)[CH:10]=[CH:9][C:8]=1[Cl:11]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 9032Potassium CyanideHCID 70621931-(3,4-Dichlorophenyl)-2-hydroxyethan-1-one

Product 1

HCID 129929604-(3,4-Dichlorophenyl)-2-oxazoloneYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-hydroxy-3′,4′-dichloroacetophenone (10.3 g), potassium cyanide (8.1 g) and 2-propanol (100 ml) was heated to 50° C., to which was added dropwise acetic acid (6.0 g) gradually and stirred at 50° C. for 2 hours. The reaction mixture was concentrated and poured into ice water (200 ml). The solid precipitates were filtered, washed with water, and air-dried to give crystals of 4-(3′,4′-dichlorophenyl)-2-oxazolone (6.0 g, 52%). Recrystallization from tetrahydrofuran-hexane gave pale yellow prisms. Melting point 262-263° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into ice water (200 ml)
  3. customThe solid precipitates
  4. filtrationwere filtered
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-72c304d992134ad2be62ddca8c49d9b6
Source dataset
uspto-grants-2003_08
Patent number
US06605629B1

Linked notes

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