Sodium Carbonate → 5-Methyl-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalen-5-yl formate

HRID 1759495Notes

Reaction equation

HRID 1759495 reaction equation
[CH3:1][C:2]1([OH:13])[CH2:11][CH2:10][CH2:9][CH:8]2[CH:3]1[CH:4]1[CH2:12][CH:7]2[CH:6]=[CH:5]1.[C:14]([O-])([O-])=[O:15].[Na+].[Na+]>>[CH:14]([O:13][C:2]1([CH3:1])[CH2:11][CH2:10][CH2:9][CH:8]2[CH:3]1[CH:4]1[CH2:12][CH:7]2[CH:6]=[CH:5]1)=[O:15]

Participants

3

Reactant 2

HCID 10340Sodium CarbonateHCID 21349241HCID 21349241, compound

Product 1

HCID 441505255-Methyl-1,4,4a,5,6,7,8,8a-octahydro-1,4-methanonaphthalen-5-yl formateYield 58%

Procedure

7.4 g (0.042 mole) of 3-methyl-tricyclo[6.2.1.02,7 ]undec-9-en-3-ol--see Example 1--were then added to the above mixture, and the whole mixture was stirred for 3 days at room temperature. The obtained mixture was then decomposed by the addition of 100 ml of a saturated aqueous solution of Na2CO3, extracted with ether (3×50 ml), washed with water (3×50 ml) and dried over Na2SO4. After evaporation 8 g of crude material were obtained which, by distillation at 0.02 Torr, provided the desired compound in a 58% yield.

Workup

  1. additionwere then added to the above mixture
  2. extractionextracted with ether (3×50 ml)
  3. washwashed with water (3×50 ml)
  4. dry with materialdried over Na2SO4
  5. customAfter evaporation 8 g of crude material
  6. customwere obtained which
  7. distillationby distillation at 0.02 Torr

Sources & evidence

ORD record
ord-23b59d2d73b24349822bbccbabd7520a
Source dataset
uspto-grants-1982_07
Patent number
US04341666

Reaction notes

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