Sodium Acetate → HCID 14692980, compound

HRID 1608073Notes

Reaction equation

HRID 1608073 reaction equation
[CH3:1][CH:2]([OH:17])[CH2:3][C:4](=[CH2:16])[CH:5]1[C:10]([CH3:12])([CH3:11])[CH2:9][C:8]([CH3:13])=[CH:7][C:6]1([CH3:15])[CH3:14].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>ClCCl>[CH3:14][C:6]1([CH3:15])[CH:7]=[C:8]([CH3:13])[CH2:9][C:10]([CH3:11])([CH3:12])[CH:5]1[C:4](=[CH2:16])[CH2:3][C:2](=[O:17])[CH3:1]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 14692981HCID 14692981, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 14692980HCID 14692980, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of α,2,2,4,6,6-hexamethyl-γ-methylene-3-cyclohexene-1-propanol (2.36 g, 0.01 mol) in dichloromethane (10 mL) was added over a 30 min period to a mixture of pyridinium chlorochromate (3.25 g, 0.015 mol), sodium acetate (2.30 g, 0.03 mol) and dichloromethane (15 mL) at 25° C. The mixture was filtered and the filtrate washed with water (100 mL) and 5% sodium carbonate solution (100 mL). The solvents were evaporated and the residue chromatographed to provide after kugelrohr distillation 1.75 g (75% yield) of 4-(2,2,4,6,6-pentamethyl-3-cyclohexen-1-yl)-4-penten-2-one (GLC purity: 94%). 1H-NMR δ0.93 (3H, s) 0.95 (3H, s), 1.02 (6H, s), 1.62 (3H, s), 1.6-1.8 (2H, m), 1.97 (1H, s), 2.18 (3H, s), 3.15 (2H, s), 5.05 (2H, broad s); IR (film) vmax 2950, 1710, 1630, 1430, 1380, 1350 cm-1 ; MS m/e 234, 219, 201, 191, 176, 161, 149, 123, 96.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate washed with water (100 mL) and 5% sodium carbonate solution (100 mL)
  3. customThe solvents were evaporated
  4. customthe residue chromatographed
  5. customto provide

Sources & evidence

ORD record
ord-ba3703a187244c8ebfccdf63384e70f6
Source dataset
uspto-grants-1989_09
Patent number
US04868339

Reaction notes

Loading…