Sodium Bicarbonate → 41429-52-1

HRID 1065142Notes

Reaction equation

HRID 1065142 reaction equation
O=[C:2]1[CH2:11][CH2:10][C:9]2([OH:12])[C:4]3([CH3:16])[CH2:5][CH2:6][CH:7]([CH2:15][CH:3]13)[C:8]2([CH3:14])[CH3:13].C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:13][C:8]1([CH3:14])[C:9]2([OH:12])[CH2:10][CH:11]=[CH:2][CH:3]3[CH2:15][CH:7]1[CH2:6][CH2:5][C:4]23[CH3:16]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20541497HCID 20541497, compound

Product 1

HCID 1468225041429-52-1Yield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

9.3 mg of N-toluenesulphonylhydrazide was added to a solution of 11.1 mg of 1,2,3,4,4a,5,6,7,8,8a-decahydro-2-oxo-4a-hydroxy-5,5,8a-trimethyl-1,6-methanonaphthalene in hot acetic acid. The mixture was refluxed for 10 minutes, subsequently poured into saturated aqueous NaHCO3 solution, extracted with CH2Cl2 and evaporated. The solution of the residue in 4 ml of ether was treated slowly at 25° C. with a 1-N solution of methyllithium in ether (0.225 ml), then stirred at 25° C. under argon, then poured into water and extracted with CH2Cl2. Chromatography (SiO2 /CH2Cl2) and sublimation at 100°-120° C. gave (+)-norpatchoulenol (m.p. 135°-141° C., 6.8 mg, 68% yield).

Workup

  1. temperatureThe mixture was refluxed for 10 minutes
  2. extractionextracted with CH2Cl2
  3. customevaporated
  4. additionThe solution of the residue in 4 ml of ether was treated slowly at 25° C. with a 1-N solution of methyllithium in ether (0.225 ml)
  5. additionpoured into water
  6. extractionextracted with CH2Cl2

Sources & evidence

ORD record
ord-10222efa7c8b4dc7a5531dd0c859bafc
Source dataset
uspto-grants-1982_05
Patent number
US04328352

Reaction notes

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