HCID 15105986, compound → HCID 22164638, compound

HRID 1032634Notes

Reaction equation

HRID 1032634 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][OH:12])[CH2:3]1.[H][H]>C(O)C>[CH3:1][C:2]1([CH3:13])[CH2:3][CH:4]([CH2:11][OH:12])[CH:5]2[CH:10]1[CH2:9][CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 15105986HCID 15105986, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 22164638HCID 22164638, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.3 g (64 mmol) of 1,1-dimethyl-3-hydroxymethylindane (IX), 3 g of 5% luthenium-carbon (manufactured by Engerhard Industries Corp.), and 300 ml of ethanol was placed in a 100 ml autoclave. After internal air was displaced by hydrogen, the mixture was heated at an initial hydrogen pressure of 100 kg/cm2. The reaction temperature reached 140° C. 1 hour after the heating was started. The absorption of hydrogen terminated when the reaction was continued at this temperature for 7 hours. After cooling, the pressure was released and the catalyst was separated out by filtration. The filtrate was distilled under reduced pressure to produce 9.7 g (53 mmol) of the title compound (Ic) at a yield of 83%. Capillary gas chromatography analysis revealed that the compound is comprised of two major components each having a peak of which the area ratio was 59:41.

Workup

  1. customreached 140° C
  2. custom1 hour
  3. customThe absorption of hydrogen
  4. customterminated when the reaction
  5. temperatureAfter cooling
  6. customthe catalyst was separated out by filtration
  7. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-c8a3703944b74df98e4dd797cf323d34
Source dataset
uspto-grants-1990_09
Patent number
US04959349

Reaction notes

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