Dichloromethane → 4-(5-Chloro-6-methylene-2,2,3-trimethylcyclohexyl)-3-buten-2-one

HRID 1680118

Reaktionsgleichung

Reaktionsgleichung von HRID 1680118
Cl[O-].[Na+].[CH3:4][CH:5]1[C:10]([CH3:12])([CH3:11])[CH:9](/[CH:13]=[CH:14]/[C:15]([CH3:17])=[O:16])[C:8]([CH3:18])=[CH:7][CH2:6]1.C(Cl)[Cl:20].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[Cl:20][CH:7]1[C:8](=[CH2:18])[CH:9]([CH:13]=[CH:14][C:15](=[O:16])[CH3:17])[C:10]([CH3:11])([CH3:12])[CH:5]([CH3:4])[CH2:6]1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 5371002alpha-IroneHCID 23665760Sodium Hypochlorite

Produkt 1

HCID 572925504-(5-Chloro-6-methylene-2,2,3-trimethylcyclohexyl)-3-buten-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of commercial bleach (42.6 ml of a 5.25% solution of sodium hypochlorite), α-irone (6.24 g), and methylene chloride (200 ml) was added a solution of potassium phosphate (monobasic) (8.16 g) in water (40 ml) during a 30 minute period. The mixture was stirred for 1 hour at 25°. The methylene chloride solution was washed with sodium bicarbonate solution and evaporated to give 7.3 g of crude product. Purification by column chromatography gave 4.59 g of 4-(5-chloro-6-methylene-2,2,3-trimethylcyclohexyl)-3-buten-2-one. NMR (CDCl3) δ0.70-0.78 (2H, d, J=5 Hz, >CHCH3), 0.90, 0.93 and 0.99 (6H, 3s, >C(CH3)2), 0.9-1.3 (1H, m, >CHCH3), 1.5-2.1 (2H, m, --CH2 --), 2.25, 2.26 and 2.28 (3H, 3s, --COCH3), 2.67 and 2.83 (1H, 2s, >CH--CH=CH--), 4.6-4.9 (1H, m, >CHCl), 4.93 and 5.12 (2H, 2s, >C=CH2, 5.8-6.3 (1H, m, --CH=CH--CO--), 6.6-7.6 (1H, m, --CH=CHCO--). IR (film) ν max 2960, 1695, 1675, 1620, 1460, 1430 cm-1. MS m/e 207, 163.

Aufarbeitung

  1. washThe methylene chloride solution was washed with sodium bicarbonate solution
  2. customevaporated
  3. customto give 7.3 g of crude product
  4. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1f95812efb054602b25908962bc56c30
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04272412

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