Acetone → HCID 10330105, compound

HRID 654667Notes

Reaction equation

HRID 654667 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12](=[O:14])[CH3:13])=[CH:9][CH:8]=[CH:7]2.[BH4-].[Na+].CC(C)=O>C(O)C>[OH:14][CH:12]([C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([OH:1])=[CH:3][CH:4]=[CH:5]2)[CH3:13]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5988671-(8-Hydroxynaphthalen-1-yl)ethanoneHCID 4311764Sodium borohydride2×

Product 1

HCID 10330105HCID 10330105, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1040 g of 8'-hydroxy-1'-acetonaphthone was dissolved in 8.5 liters of ethanol, to which 131 g of sodium borohydride was added while ice-cooling in order not to allow the temperature of the reaction solution to exceed 30° C. After agitation for 30 minutes at room temperature, excess sodium borohydride was decomposed with 1 liter of acetone. The reaction solution was concentrated under reduced pressure, after which 4 liters of 1N hydrochloric acid was added, followed by extraction with ethyl acetate. The resultant organic phase was washed with a saturated saline solution to remove the excess acid. After drying with anhydrous magnesium sulfate, the solvent was distilled off and a small amount of hexane was added to the resultant residue for crystallization. The crystals were collected by filtration to obtain 1000 g of the captioned compound as light brown crystals.

Workup

  1. additionwas added while ice-
  2. temperaturecooling in order not
  3. customto exceed 30° C
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. additionafter which 4 liters of 1N hydrochloric acid was added
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe resultant organic phase was washed with a saturated saline solution
  8. customto remove the excess acid
  9. dry with materialAfter drying with anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off
  11. additiona small amount of hexane was added to the resultant residue for crystallization
  12. filtrationThe crystals were collected by filtration

Sources & evidence

ORD record
ord-ab6be7758462426a864b5a99b89cec84
Source dataset
uspto-grants-1992_07
Patent number
US05134111

Reaction notes

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