Dihydro-alpha-ionone → HCID 20531507, compound

HRID 1660571Notes

Reaction equation

HRID 1660571 reaction equation
[Br-:1].[Na+].Cl[O-].[Na+].[CH3:6][C:7]1[CH:12]([CH2:13][CH2:14][C:15]([CH3:17])=[O:16])[C:11]([CH3:19])([CH3:18])[CH2:10][CH2:9][CH:8]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O.C(Cl)Cl>[Br:1][CH:8]1[C:7](=[CH2:6])[CH:12]([CH2:13][CH2:14][C:15](=[O:16])[CH3:17])[C:11]([CH3:19])([CH3:18])[CH2:10][CH2:9]1

Participants

7

Reactant 4

HCID 35821Dihydro-alpha-iononeHCID 62657Potassium Phosphate, Tribasic2×HCID 253881Sodium Bromide2×HCID 23665760Sodium Hypochlorite

Product 1

HCID 20531507HCID 20531507, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 6344DichloromethaneSolvent

Procedure

A solution of sodium bromide (6.17 g) in water (10 ml) and commercial bleach (31.2 ml of a solution of sodium hypochlorite) were stirred together for 5 minutes and a solution of dihydro-α-ionone (3.88 g) in methylene chloride was added. Then a solution of potassium phosphate (monobasic) (5.44 g) in water (30 ml) was added during 30 minutes. After stirring for 50 minutes at 25° a solution of sodium bromide (2.05 g) and commercial bleach (10 ml) was added, followed by a solution of potassium phosphate (monobasic) (2.72 g) in water (10 ml) and the reaction mixture stirred for 15 minutes at 25°. The methylene chloride solution was washed with sodium bicarbonate solution and the solvent evaporated to provide the crude product (5.86 g). Column chromatography gave 1.87 g of 4-(5-bromo-6-methylene-2,2-dimethylcyclohexyl)-2-butanone. NMR (CDCl3) δ0.93 (6H, s, >C(CH3)2), 0.9-2.6 (9H, m), 2.12 (3H, s, --COCH3), 4.6-5.1 (1H, m, >CHBr), 4.76 and 5.28 (2H, 2s, >C=CH2), 4.68 and 5.20 (2H, 2s, >C=CH2, minor isomer; isomer ratio 3/1). IR (film) νmax 2960, 1720, 1675, 1650, 1455, 1360.

Workup

  1. additionwas added
  2. washThe methylene chloride solution was washed with sodium bicarbonate solution
  3. customthe solvent evaporated
  4. customto provide the crude product (5.86 g)

Sources & evidence

ORD record
ord-44aaad8b1487466e9e846d86f18c8b3b
Source dataset
uspto-grants-1981_12
Patent number
US04308401

Reaction notes

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