Hydrochloric Acid → HCID 20337424, compound

HRID 1706253Notes

Reaction equation

HRID 1706253 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH:9]([CH2:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:10].[C:20]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C:24]1=O)(=O)[CH3:21].Cl.[C:31](=[O:34])(O)[O-].[Na+].[C:36]([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:31]([O:1][C:2]1[C:3]([CH:9]([CH3:10])[CH2:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:4][C:5]2[O:8][CH:20]([CH3:21])[C:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=3[C:6]=2[CH:7]=1)(=[O:34])[CH3:36]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 134002-AcetylcyclohexanoneHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 20337452HCID 20337452, compound

Product 1

HCID 20337424HCID 20337424, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 25.6 g. (0.10 mole) 2-(2',5'-dihydroxyphenyl)-5-phenylpentane and 14.0 g. (0.10 mole) of 2-acetylcyclohexanone in 75 ml. of glacial acetic acid is cooled to 15° C. and anhydrous hydrogen chloride gas is passed through the solution for 30 minutes. The resulting red solution is allowed to warm to room temperature and stirred for four days. The solution is then added to a suspension of 40 g. of sodium bicarbonate in 500 ml. of methanol at -5° C. and the resulting mixture is treated portionwise with 2.0 g. of sodium cyanoborohydride. The mixture is concentrated in vacuo, the residue diluted with water and the aqueous solution extracted with ether (3×300 ml.). The combined extracts are washed with water, 5% aqueous sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. The residue is dissolved in a solution of 350 ml. of pyridine and 140 g. of acetic anhydride, refluxed for 15 minutes, then allowed to stir at 25° C. overnight. The resulting mixture is again evaporated in vacuo and the residue dissolved in hexane. The solution is washed with water, dilute hydrochloric acid and water, dried (Na2SO4) and concentrated in vacuo to afford crude dl-7,8,9,10-tetrahydro-2-acetoxy-6-methyl-3-(1-methyl-4-phenylbutyl)-6H-dibenzo[b,d]pyran which is purified by chromatography on silica gel.

Workup

  1. additionThe solution is then added to a suspension of 40 g
  2. concentrationThe mixture is concentrated in vacuo
  3. additionthe residue diluted with water
  4. extractionthe aqueous solution extracted with ether (3×300 ml.)
  5. washThe combined extracts are washed with water, 5% aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue is dissolved in a solution of 350 ml
  9. temperatureof acetic anhydride, refluxed for 15 minutes
  10. stirringto stir at 25° C. overnight
  11. customThe resulting mixture is again evaporated in vacuo
  12. dissolutionthe residue dissolved in hexane
  13. washThe solution is washed with water, dilute hydrochloric acid and water
  14. dry with materialdried (Na2SO4)
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29f1a5628a374b27af17948a24738f60
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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