Acetone → 2,4,6-Trimethyl-2,3-dihydro-1H-inden-1-ol

HRID 2425305Notes

Reaction equation

HRID 2425305 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH3:12])=[CH:7][C:8]=2[CH3:11])[C:3]1=[O:13].[BH4-].[Na+].CC(C)=O.O>CCO>[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH3:12])=[CH:7][C:8]=2[CH3:11])[CH:3]1[OH:13]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 4311764Sodium borohydrideHCID 12195664HCID 12195664, compound

Product 1

HCID 672589662,4,6-Trimethyl-2,3-dihydro-1H-inden-1-olYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

37.48 g of 2,4,6-trimethyl-indan-1-one (0.215 mol) were dissolved in 200 mL of EtOH in a 500 mL, 3-neck rounded bottom flask equipped with a magnetic stirring bar, a thermometer and a reflux condenser. NaBH4 (15.01 g, 0.397 mol) was then slowly added keeping the temperature below 20° C. during the addition. The light yellow suspension was stirred at r.t. for 18 h. Then 100 mL of acetone were cautiously added (careful: exothermic reaction!) and subsequently the solvents removed giving a white solid. The latter was treated with 100 mL of water and extracted with toluene (2×150 mL). The water phase was further extracted with toluene, the organic phases were combined and washed with a 10% aqueous solution of NH4Cl. After washing, the organic phase was dried over Na2SO4, filtered and evaporated to give 35.57 g of a yellow sticky solid: its 1H-NMR analysis showed the target product as 1.4/1 mixture of two diastereoisomers, contaminated by 5% wt. of starting indanone (yield 89.2%). The product was used as such in the next step without further purification.

Workup

  1. customequipped with a magnetic stirring bar
  2. customthe temperature below 20° C.
  3. additionduring the addition
  4. custom(careful: exothermic reaction!)
  5. customsubsequently the solvents removed
  6. customgiving a white solid
  7. extractionextracted with toluene (2×150 mL)
  8. extractionThe water phase was further extracted with toluene
  9. washwashed with a 10% aqueous solution of NH4Cl
  10. washAfter washing
  11. dry with materialthe organic phase was dried over Na2SO4
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-3c236e176cfe45b2bb8deb333a70c0c2
Source dataset
uspto-grants-2011_06
Patent number
US07964679B2

Reaction notes

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