5,6-Dimethyl-1-indanone → HCID 18402889, compound

HRID 1017138Notes

Reaction equation

HRID 1017138 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[CH2:6][CH2:5]2.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[CH:7]([OH:12])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 278785,6-Dimethyl-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 18402889HCID 18402889, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

A 1 L three-neck round bottom flask equipped with a condenser, mechanical stirrer, nitrogen inlet and a thermometer was charged with 5,6-dimethyl-1-indanone (21.65 g, 0.133 mol) and ethanol (450 mL). The mixture was heated with stirring to 45° C. and sodium borohydride (15.2 g, 0.40 mol) was added incrementally over 10 minutes. The reaction mixture was then heated at reflux for 18 hours, cooled, quenched in 5% HCl (1 L ice-water), and extracted with diethyl ether (500 mL). The organic phase was separated, washed with water (3×500 mL), dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure to yield 5,6-dimethyl-1-indanol (23.0 g) as an amber oil. 1HNMR (CD2Cl2, 500 MHz) δ7.12 (s, 1H); 7.01 (s, 1H); 4.81 (m, 1H); 2.95 (m, 1H); 2.72 (m, 1H); 2.28 (m, 1H); 2,26 (s, 3H); 2.23 (s, 3H).

Workup

  1. customA 1 L three-neck round bottom flask equipped with a condenser, mechanical stirrer, nitrogen inlet
  2. temperatureThe mixture was heated
  3. temperatureThe reaction mixture was then heated
  4. temperatureat reflux for 18 hours
  5. temperaturecooled
  6. customquenched in 5% HCl (1 L ice-water)
  7. extractionextracted with diethyl ether (500 mL)
  8. customThe organic phase was separated
  9. washwashed with water (3×500 mL)
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-1f983cc6bb1142bfa7ec5ca9c46968c4
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

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