Dichloromethane → 4-(5-Chloro-6-methylene-2,2-dimethylcyclohexyl)-2-butanone

HRID 1680115Notes

Reaction equation

HRID 1680115 reaction equation
Cl[O-].[Na+].[CH3:4][C:5]1[CH:10]([CH2:11][CH2:12][C:13]([CH3:15])=[O:14])[C:9]([CH3:17])([CH3:16])[CH2:8][CH2:7][CH:6]=1.C(Cl)[Cl:19].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[Cl:19][CH:6]1[C:5](=[CH2:4])[CH:10]([CH2:11][CH2:12][C:13](=[O:14])[CH3:15])[C:9]([CH3:17])([CH3:16])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 35821Dihydro-alpha-iononeHCID 62657Potassium Phosphate, TribasicHCID 23665760Sodium Hypochlorite

Product 1

HCID 199372844-(5-Chloro-6-methylene-2,2-dimethylcyclohexyl)-2-butanoneYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of commercial bleach (28.5 ml of a 5.25% solution of sodium hypochlorite) α-dihydro-ionone (3.88 g) and methylene chloride (110 ml) was added a solution of potassium phosphate (monobasic) (5.44 g) in water (40 ml) during a 15 minute period. The mixture was stirred for 1 hour at 25°. The methylene chloride solution was washed with sodium bicarbonate solution, the solvent evaporated, and the residue distilled to give 2.81 g (61% yield) of 4-(5-chloro-6-methylene-2,2-dimethylcyclohexyl)-2-butanone, bp 101°-106°, 0.2 mm. NMR (CDCl3) δ0.85 and 0.95 (6H,2s,>C(CH3)2), 0.9-2.6 (9H, m), 2.10 (3H, s, --COCH3), 4.36-4.55 (1H, t, J=6 Hz,>CHCl), 4.76 and 5.33 (2H,2s,>C=(CH2). IR (film) γmax 2950, 1720, 1675, 1650, 1455, 1360. MS m/e 193, 175, 159, 134, 119.

Workup

  1. washThe methylene chloride solution was washed with sodium bicarbonate solution
  2. customthe solvent evaporated
  3. distillationthe residue distilled

Sources & evidence

ORD record
ord-6b330c1dba09481bb61e1ede705cd98c
Source dataset
uspto-grants-1981_06
Patent number
US04272412

Reaction notes

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