Sodium Acetate → HCID 67794808, compound

HRID 1651056Notes

Reaction equation

HRID 1651056 reaction equation
C1(C)C=CC(S(OC[CH:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3C=[CH:15][C:14]3[CH:23]=[CH:24][CH:25]=[CH:26][C:13]2=3)(=O)=O)=CC=1.[C:28]([O-:31])(=O)[CH3:29].[Na+]>C(O)(=O)C>[OH:31][C:28]1[C:29]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:18]=[CH:12][C:13]2[CH:26]=[CH:25][CH:24]=[CH:23][C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 86743948HCID 86743948, compound

Product 1

HCID 67794808HCID 67794808, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-p-toluenesulphonyloxymethyldibenzo[a,d]cycloheptene (17 g) in glacial acetic acid (150 ml) was added anhydrous sodium acetate (8.2 g) and the solution refluxed with stirring for 4 h. The solvents were removed in vacuo, the residue dissolved in methanol (100 ml), cooled to 0° C. and enough solid potassium hydroxide added to give pH 14. The suspension was stirred at room temperature for 2 h. then the methanol was removed in vacuo and the residue Partitioned between ether (200 ml) and water (50 ml). The organic layer was washed three times with water (50 ml), then dried and evaporated to qive the crude alcohol which was crystallised from n-hexane/5% ethyl acetate (10.2 g), mp 120°-1° C.

Workup

  1. temperaturethe solution refluxed
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue dissolved in methanol (100 ml)
  4. additionenough solid potassium hydroxide added
  5. customto give pH 14
  6. stirringThe suspension was stirred at room temperature for 2 h.
  7. customthe methanol was removed in vacuo
  8. customthe residue Partitioned between ether (200 ml) and water (50 ml)
  9. washThe organic layer was washed three times with water (50 ml)
  10. customdried
  11. customevaporated
  12. customwas crystallised from n-hexane/5% ethyl acetate (10.2 g), mp 120°-1° C.

Sources & evidence

ORD record
ord-f2a38b146d47433ca619855c6cf7c0ed
Source dataset
uspto-grants-1990_05
Patent number
US04927819

Reaction notes

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