Hydrochloric Acid → 9-(4-tert-Butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthalene

HRID 271798

Reaction equation

HRID 271798 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[CH:20]=[C:19]3[C:27](=O)[CH:28]([CH3:30])[CH2:29][C:18]=23)=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].Cl.C1C=CC=CC=1.CCOC(C)=O>CCOCC>[C:7]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:26]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=3[CH:20]=[C:19]3[CH:27]=[C:28]([CH3:30])[CH2:29][C:18]=23)=[CH:15][CH:16]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 21583983Benzene ethyl acetateHCID 687464074-(4-t-butylphenyl)-2-methyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-1-one

Product 1

HCID 866134919-(4-tert-Butylphenyl)-2-methyl-5,6,7,8-tetrahydro-1H-cyclopenta[b]naphthaleneYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

LiAlH4 (0.95 g, 25 mmol) was added at −20° C. to the solution of 4-(4-tert-Butylphenyl)-2-methyl-2,3,5,6,7,8-hexahydro-1H-cyclopenta[b]naphthalen-1-one (16.6 g, 50 mmol) in Et2O (150 ml). Resulting mixture was allowed to warm to room temperature and stirred for additional 1 h. Then 5% HCl (100 ml) was added, the resulting mixture was extracted by Et2O (3 times of 50 ml). Combined organic phases were washed by water, dried over MgSO4 and evaporated. Benzene (300 ml) and p-TSA (0.5 g) were added, and resulting solution was refluxed with Dean Stark head (control by TLC, benzene/EtOAc 4:1) within 4 h. Then the resulting solution was washed by water, aq. KHCO3, water, dried over MgSO4, passed through silica gel and evaporated giving 12.8 g (81%) of product.

Workup

  1. customResulting mixture
  2. extractionthe resulting mixture was extracted by Et2O (3 times of 50 ml)
  3. washCombined organic phases were washed by water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. additionBenzene (300 ml) and p-TSA (0.5 g) were added
  7. customresulting solution
  8. washThen the resulting solution was washed by water, aq. KHCO3, water
  9. dry with materialdried over MgSO4
  10. customevaporated

Sources & evidence

ORD record
ord-998d5d917f9c43faa2af671ebe81d03d
Source dataset
uspto-grants-2008_11
Patent number
US07452949B2

Linked notes

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