Potassium Hydroxide → HCID 136227081, compound

HRID 1606022Notes

Reaction equation

HRID 1606022 reaction equation
[OH:1][C:2]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=O.[OH-:18].[K+].Cl.[NH2:21]O>C(O)C.O>[OH:1][C:2]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:3]=1[C:4](=[N:21][OH:18])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 223484(4-Chlorophenyl)(2-hydroxy-3-methylphenyl)methanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 136227081HCID 136227081, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The ketone of Example 30 (7.5g,0.03mole) in ethanol (18ml) was added with stirring to a solution of (85%) potassium hydroxide (20.74g, 0.3mole) in water (85ml) at 10°C, this colloidal solution was treated with solid hydroxylamine hydrochloride (8.54g,0.12 mole) and stirred overnight. The solution was acidified with 5NHCl to give a solid, which was filtered, washed with water and stirred for 45 minutes, with 5% Na2CO3 solution (30.5ml), to remove unwanted oxime stereoisomer, filtered, washed with 5% Na2CO3 solution (100ml) and then with water until free of alkali. The dried solid had m.p. 175°-177°C. Recrystallisation from 54% benzene-light petroleum (b.p. 60°-80°C) mixture gave the oxime, m.p. 178°C ("bonded isomer") 5.45g.

Workup

  1. customto give a solid, which
  2. filtrationwas filtered
  3. washwashed with water
  4. stirringstirred for 45 minutes, with 5% Na2CO3 solution (30.5ml)
  5. customto remove unwanted oxime stereoisomer
  6. filtrationfiltered
  7. washwashed with 5% Na2CO3 solution (100ml)
  8. customRecrystallisation from 54% benzene-light petroleum (b.p. 60°-80°C) mixture

Sources & evidence

ORD record
ord-860ef2ddda7349d18dad436395459e7a
Source dataset
uspto-grants-1976_04
Patent number
US03951999

Reaction notes

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