HCID 21434893, compound → HCID 21434888, compound

HRID 1415261Notes

Reaction equation

HRID 1415261 reaction equation
[OH:1][CH:2]1[CH:11]([CH:12]([CH3:14])[CH3:13])[CH2:10][C:9]2[CH:5]([CH2:6][CH2:7][C:8]=2[CH3:15])[C:4](=[CH2:16])[CH2:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH:12]([CH:11]1[CH2:10][C:9]2[CH:5]([CH2:6][CH2:7][C:8]=2[CH3:15])[C:4](=[CH2:16])[CH2:3][C:2]1=[O:1])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 21434893HCID 21434893, compoundHCID 131709961Jones' reagent

Product 1

HCID 21434888HCID 21434888, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution, cooled to -10°, of 1.10 g of 6-hydroxy-7-isopropyl-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene (isomer A) in 50 ml of acetone was treated within 10 minutes with 2 ml of Jones reagent (5.3 mM CrO3) and the reaction mixture obtained then poured on to ice-cold bicarbonate solution. Extraction with ether, washing the extracts with bicarbonate solution and water, drying with sodium sulphate, concentration and distillation under reduced pressure yielded 990 mg (yield 90%) of 7-isopropyl-1-methyl-4-methylen-6-oxo-2,3,3a,4,5,6,7,8-octahydroazulene (isomer A) in the form of a colourless oil; b.p.0.01 ca 75°; IR(film): νmax = 3100, 1708, 1642, 1460, 1440, 1390, 1370, 1255, 1205, 1140, 1090, 1062, 1005, 970, 900, 800 cm-1. The compound has a sweet, spicy, woody odour. In analogous manner there were obtained from 1.10 g of the B-isomer of 6-hydroxy-7-isopropyl-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene, 890 g (yield 81%) of the B-isomer of the corresponding 6-oxo-octahydroazulene; b.p.0.01 ca 75°; IR(film): νmax = 1390, 1710, 1642, 1470/60/40, 1390, 1370, 1265, 1180, 1092, 1062, 1000, 970, 900 cm-1. The compound has a fresh woody, slighly spicy, camphorous odour.

Workup

  1. customthe reaction mixture obtained
  2. additionthen poured on to ice-cold bicarbonate solution
  3. extractionExtraction with ether
  4. washwashing the extracts with bicarbonate solution and water
  5. dry with materialdrying with sodium sulphate, concentration and distillation under reduced pressure

Sources & evidence

ORD record
ord-1fe63f7535bb41f5b123f48a2d642195
Source dataset
uspto-grants-1977_01
Patent number
US04003951

Reaction notes

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