Acetic Acid → HCID 21568766, compound

HRID 1579553Notes

Reaction equation

HRID 1579553 reaction equation
[CH3:1][CH:2]([C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[C:14]([CH:16]=1)[OH:15])[CH:3]([CH3:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:18]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=O)(=O)[CH3:19].Cl.[C:29](O)(=[O:31])[CH3:30]>>[C:29]([O:17][C:12]1[C:13]2[CH:18]([CH3:19])[C:21]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=3[O:15][C:14]=2[CH:16]=[C:10]([CH:2]([CH3:1])[CH:3]([CH3:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:11]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 134002-AcetylcyclohexanoneHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diol

Product 1

HCID 21568766HCID 21568766, compound

Procedure

A solution of 26.2 g. of 5-(1,2-dimethylheptyl)resorcinol and 16.5 g. of 2-acetylcyclohexanone in 150 ml. of acetic acid is cooled to 15° and saturated with hydrogen chloride gas. The mixture is allowed to warm to 25°, stirred for 48 hours and then quenched by pouring into 500 ml. of methanol at 0° and adding 40 g. of sodium bicarbonate to the methanol solution. Sodium cyanoborohydride is then added to the reaction mixture until the bright orange color is dissipated. The solution is concentrated in vacuo, water is added to the residue and the aqueous mixture is extracted with ether. The extract is washed with water and 5% aqueous sodium bicarbonate, dried (MgSO4) and concentrated to give a residue which is chromatographed on silica. The less polar fraction is collected and dissolved in 150 ml. of pyridine. Acetic anhydride (64 g.) is added and the solution is refluxed 10 minutes then allowed to stir at 25° for 18 hours. The mixture is concentrated in vacuo, the residue is dissolved in hexane and the hexane solution is washed with water, dilute hydrochloric acid and water, dried (Na2SO4) and concentrated to give a residue which is chromatographed on silica with 1:1 methylene chloride-petroleum ether to give 1-acetoxy-3-(1,2-dimethylheptyl)-5,6,7,8-tetrahydro-9-methylxanthene.

Workup

  1. temperatureto warm to 25°
  2. customquenched
  3. additionby pouring into 500 ml
  4. additionof methanol at 0° and adding 40 g
  5. additionSodium cyanoborohydride is then added to the reaction mixture until the bright orange color
  6. concentrationThe solution is concentrated in vacuo, water
  7. additionis added to the residue
  8. extractionthe aqueous mixture is extracted with ether
  9. washThe extract is washed with water and 5% aqueous sodium bicarbonate
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated
  12. customto give a residue which
  13. customis chromatographed on silica
  14. customThe less polar fraction is collected
  15. dissolutiondissolved in 150 ml
  16. additionAcetic anhydride (64 g.) is added
  17. temperaturethe solution is refluxed 10 minutes
  18. stirringto stir at 25° for 18 hours
  19. concentrationThe mixture is concentrated in vacuo
  20. dissolutionthe residue is dissolved in hexane
  21. washthe hexane solution is washed with water, dilute hydrochloric acid and water
  22. dry with materialdried (Na2SO4)
  23. concentrationconcentrated
  24. customto give a residue which
  25. customis chromatographed on silica with 1:1 methylene chloride-petroleum ether

Sources & evidence

ORD record
ord-cf19934e2e4b4af892b181004c3ea3f8
Source dataset
uspto-grants-1976_01
Patent number
US03931232

Reaction notes

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