Sodium Carbonate → 3-Methyl-8-methylidene-1,2,4,5,6,7,8,8a-octahydroazulen-6-ol

HRID 1415256Notes

Reaction equation

HRID 1415256 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][C:6]([CH3:9])=[C:5]1[CH2:10][CH2:11][CH:12]=[O:13])([CH3:3])=[CH2:2].[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>C1C=CC=CC=1.CCOCC>[OH:13][CH:12]1[CH2:11][CH2:10][C:5]2[CH:4]([CH2:8][CH2:7][C:6]=2[CH3:9])[C:1](=[CH2:3])[CH2:2]1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 24287Tin tetrachlorideHCID 124807202-(2-Formylethyl)-3-isopropenyl-1-methyl-cyclopent-1-ene

Product 1

HCID 214348863-Methyl-8-methylidene-1,2,4,5,6,7,8,8a-octahydroazulen-6-olYield 72%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution, cooled to 0°, of 57 g of 3-isopropenyl-1-methyl-2-(3-oxopropyl)-1-cyclopentene in 3 l of absolute benzene and 800 ml of absolute ether were added dropwise under a nitrogen atmosphere within 30 minutes 900 ml of a 0.5 M solution of tin tetrachloride in benzene. The mixture was stirred for a further 30 minutes at 5°, whereby it became red coloured, then treated at 0° with saturated sodium carbonate solution up to an alkaline reaction and suction filtered. The benzene solution was washed with saturated sodium carbonate solution and water, dried with anhydrous sodium sulphate and evaporated under reduced pressure. The crude product obtained was fractionated on a short column with the addition of 2 g of anhydrous potash. There were obtained 41 g (yield 72%) of 6-hydroxy-1-methyl-4-methylen-2,3,3a,4,5,6,7,8-octahydroazulene; b.p.0.5 90°-92°; nD 20 = 1.5233; IR(film):νmax = 3450, 3090, 1640,1450, 1440, 1380, 1200, 1155, 1098, 1080, 1060, 1030, 942, 890, 775 cm-1. The compound has a flowery, camphorous, woody odour.

Workup

  1. filtrationfiltered
  2. washThe benzene solution was washed with saturated sodium carbonate solution and water
  3. dry with materialdried with anhydrous sodium sulphate
  4. customevaporated under reduced pressure
  5. customThe crude product obtained

Sources & evidence

ORD record
ord-06e9dd1589ab41cd85da27697c872c64
Source dataset
uspto-grants-1977_01
Patent number
US04003951

Reaction notes

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