Hydrochloric Acid → HCID 86632272, compound

HRID 2267210Notes

Reaction equation

HRID 2267210 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[C:12](C3C=CC(C(C)(C)C)=CC=3)[CH:13]=1)[C:10](=O)[CH:9](C)[CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>CCOCC>[C:1]([C:5]1[CH:6]=[CH:7][C:11]([CH3:10])=[C:12]([CH:12]2[C:13]3[C:9](=[CH:8][CH:7]=[CH:6][C:5]=3[C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[CH:11]2)[CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 67402702HCID 67402702, compound

Product 1

HCID 86632272HCID 86632272, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

5-tert-Butyl-7-(4-tert-butylphenyl)-2-methyl-1-indanone (10.37 g, 31mmol) in Et2O (150 ml) was added dropwise at 0° C. to LiAlH4 (0.6 g, 16 mmol) in Et2O (100 ml). After 1 h of stirring, 5% HCl (50 ml) was added, the organic phase was separated, the water layer was extracted in Et2O (2×50 ml). The combined organic phase was washed with aq. Na2CO3, dried over MgSO4 and evaporated. The residue was dissolved in benzene (500 ml), p-TSA (1 g) was added, the resulting mixture was refluxed for 10 min, cooled, washed with water, dried over MgSO4, evaporated and dried in vacuo. The yield was 9.9 g (near quantitative); yellow viscous oil.

Workup

  1. customthe organic phase was separated
  2. extractionthe water layer was extracted in Et2O (2×50 ml)
  3. washThe combined organic phase was washed with aq. Na2CO3
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. dissolutionThe residue was dissolved in benzene (500 ml)
  7. additionp-TSA (1 g) was added
  8. temperaturethe resulting mixture was refluxed for 10 min
  9. temperaturecooled
  10. washwashed with water
  11. dry with materialdried over MgSO4
  12. customevaporated
  13. customdried in vacuo

Sources & evidence

ORD record
ord-b9cb951fa262443dbe76f6caf53b0e72
Source dataset
uspto-grants-2010_12
Patent number
US07858717B2

Reaction notes

Loading…