Methanol → HCID 15413223, compound

HRID 2226089Notes

Reaction equation

HRID 2226089 reaction equation
[CH3:1]O.[C:3]([O:6][C:7]([CH3:9])=[CH2:8])(=[O:5])[CH3:4].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13](S(O)(=O)=O)=[CH:12][CH:11]=1.[CH3:21][CH2:22]OCC>>[C:3]([O:6][C:7]1([CH3:1])[CH2:9][CH2:22][CH2:21][CH:20]2[CH:8]1[CH:13]1[CH2:14][CH2:15][CH:10]2[CH:11]=[CH:12]1)(=[O:5])[CH3:4]

Participants

5

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 7916Isopropenyl acetate

Product 1

HCID 15413223HCID 15413223, compoundYield 34%

Procedure

A mixture of 6.0 g (31.2 mmole) of the carbinol obtained under a. above, 60 ml of isopropenyl acetate and 0.025 g of p-toluenesulfonic acid was heated to reflux during 20 h. After cooling, the mixture was taken in ether, washed with a 5% aqueous solution of sodium bicarbonate, dried and concentrated. Bulb-to-bulb distillation (about 100°/0.05 hPa) gave 2.5 g (10.7 mmole; yield 34,2%) of (±)-(1RS,2SR,3RS,7RS)-3-methyl-tricyclo [6.2.2.02,7 ]dodec-9-en-3- yl acetate.

Workup

  1. customobtained under a
  2. temperatureto reflux during 20 h
  3. temperatureAfter cooling
  4. washwashed with a 5% aqueous solution of sodium bicarbonate
  5. customdried
  6. concentrationconcentrated
  7. distillationBulb-to-bulb distillation (about 100°/0.05 hPa)

Sources & evidence

ORD record
ord-bf209084033e4804b5516b953d1507b6
Source dataset
uspto-grants-1994_09
Patent number
US05346885

Reaction notes

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