Acetone → HCID 22463177, compound

HRID 2425309Notes

Reaction equation

HRID 2425309 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=2[CH3:11])[C:3]1=[O:13].[BH4-].[Na+].CC(C)=O.[BH4-]>CCO>[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=2[CH3:11])[CH:3]1[OH:13]

Participants

6

Reactant 4

HCID 180AcetoneHCID 28123BorohydrideHCID 4311764Sodium borohydrideHCID 110951212,4,7-trimethyl-1-indanone

Product 1

HCID 22463177HCID 22463177, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

8.95 g of 2,4,7-trimethylindanone (51.4 mmol) were dissolved in 70 ml of EtOH; the solution was cooled to 0° C. and 2.00 g of NaBH4 (51.8 mmol) were added to it in small aliquots. At the end of the addition, the reaction mixture was allowed to reach ambient temperature and then heated at 50° C. for 3 hours and 30 min. The reaction mixture was cooled to 0° C., and 50 ml of acetone were slowly (careful: exothermic reaction!) added to it to deactivate the residual borohydride. All volatiles were then removed in vacuo, the white solid obtained was treated with 50 ml of 1H2O and stirred for 30 min. The organic layer was extracted with Et2O (2×100 ml), washed with H2O, dried and essiccated in vacuo to leave 9.06 g of a white solid (100%).

Workup

  1. additionAt the end of the addition
  2. customto reach ambient temperature
  3. temperatureheated at 50° C. for 3 hours and 30 min
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. custom(careful: exothermic reaction!)
  6. additionadded to it
  7. customAll volatiles were then removed in vacuo
  8. customthe white solid obtained
  9. extractionThe organic layer was extracted with Et2O (2×100 ml)
  10. washwashed with H2O
  11. customdried

Sources & evidence

ORD record
ord-9d421b647e2442d0926be3f11229ff3c
Source dataset
uspto-grants-2011_06
Patent number
US07964679B2

Reaction notes

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