Hydrochloric Acid → HCID 12113148, compound

HRID 495115Notes

Reaction equation

HRID 495115 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]1[CH3:12].[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>C1COCC1>[CH3:12][CH:3]1[C:2]([CH3:13])([CH3:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]1[OH:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 101490362,3-Dihydro-2,3,3-trimethyl-1H-inden-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 12113148HCID 12113148, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3,3,2-Trimethyl-1-indanone (9.03 g, 50 mmol) as prepared above was dissolved in THF (40 ml) and added to the suspension of LiAlH4 (3.80 g, 100 mmol, 2 equiv.) in THF (10 ml). The mixture was heated to reflux for 2 h, then cooled to 5° C. and hydrolysed via addition of 2N aq. HCl-solution. The crude product obtained after extraction with MTBE, washing with sat. aq. NaHCO3 solution and brine, drying over MgSO4 and concentrating in a rotary evaporator was distilled at 0.1 mbar/72-73° C. to yield 8.70 g (95%) of product as a colourless viscous oil. The compound was obtained as a mixture of diastereomers 87:13, the major isomer being the 1,2-trans compound upon NMR-analysis.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. customThe crude product obtained
  4. extractionafter extraction with MTBE
  5. washwashing with sat. aq. NaHCO3 solution and brine
  6. dry with materialdrying over MgSO4
  7. concentrationconcentrating in a rotary evaporator
  8. distillationwas distilled at 0.1 mbar/72-73° C.

Sources & evidence

ORD record
ord-45481bfcaefe4bbc9134f160d1ea21c6
Source dataset
uspto-grants-2009_05
Patent number
US07538243B2

Reaction notes

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