Dichloromethane → HCID 57031902, compound

HRID 1660573Notes

Reaction equation

HRID 1660573 reaction equation
Cl[O-].[Na+].[CH3:4][C:5]1[CH:10](/[CH:11]=[CH: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]([CH:11]=[CH:12][C:13](=[O:14])[CH3:15])[C:9]([CH3:17])([CH3:16])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 5282108Alpha-IononeHCID 23665760Sodium Hypochlorite

Product 1

HCID 57031902HCID 57031902, compound

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-ionone (3.84 g), and methylene chloride (330 ml) was added a solution of potassium phosphate (monobasic) (5.44 g) in water (40 ml) during a 30 minute period. The mixture was stirred for 30 minutes at 25°, the methylene chloride solution washed with sodium bicarbonate solution and evaporated to give 4.1 g of crude product. Purification by column chromatography gave 2.35 g of 4-(5-chloro-6-methylene-2,2-dimethylcyclohexyl)-3-buten-2-one. NMR (CDCl3) δ0.90 and 0.93 (6H, 2s, >C(CH3)2), 0.9-2.1 (4H, m), 2.27 (3H, s, --COCH3), 2.53 and 2.71 (1H, 2s, >CH--CH=CH--), 4.35-4.68 (1H, m, >CHCl), 4.70, 4.83, 5.15 and 5.33 (2H, 4s, >C=CH2), 5.9-6.4 (1H, m, --CH=CH--CO--), 6.7-7.3 (1H, --CH=CH--COCH3). IR (film) νmax 2960, 1695, 1675, 1630, 1450, 1430 cm -1. MS m/e 191, 149.

Workup

  1. washthe methylene chloride solution washed with sodium bicarbonate solution
  2. customevaporated
  3. customto give 4.1 g of crude product
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-58521295ace54089b86a39e6aba4c885
Source dataset
uspto-grants-1981_12
Patent number
US04308401

Reaction notes

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