Hydrochloric Acid → HCID 68504666, compound

HRID 1717644Notes

Reaction equation

HRID 1717644 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=[C:16]3[C:12]=2[CH2:13][CH:14]([CH3:24])[C:15]3=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>CCOCC>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:19]3[O:20][CH2:21][O:22][C:18]=3[CH:17]=[C:16]3[C:12]=2[CH2:13][C:14]([CH3:24])=[CH:15]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 68511202HCID 68511202, compound

Product 1

HCID 68504666HCID 68504666, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

8-(4-tert-Butylphenyl)-6-methyl-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one (30.63 g, 95 mmol) in Et2O (200 ml) was added to a cooled (−40° C.) suspension of LiAlH4 (1.08 g, 28.5 mmol) in Et2O (60 ml). The resulting mixture was allowed to warm to room temperature and stirred for additional 1.5 h. Then 2% HCl (100 ml) was added, the resulting mixture was extracted with CH2Cl2 (4×100 ml). The organic phase was washed with water, dried over MgSO4 and evaporated. The flask was sparged with argon; benzene (300 ml) and p-TSA (0.2 g) were added, and the resulting solution was refluxed with Dean-Stark head (control by TLC, benzene) for 2 h. Then the resulting yellow solution was washed with water, aq. KHCO3, water, dried over MgSO4, passed through silica gel and evaporated. The residue was recrystallized from hexane —Et2O (ca. 10:1) yielding 19.7 g (67.7%) of white crystalline product.

Workup

  1. temperaturea cooled
  2. extractionthe resulting mixture was extracted with CH2Cl2 (4×100 ml)
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe flask was sparged with argon
  7. additionbenzene (300 ml) and p-TSA (0.2 g) were added
  8. temperaturethe resulting solution was refluxed with Dean-Stark head (control by TLC, benzene) for 2 h
  9. washThen the resulting yellow solution was washed with water, aq. KHCO3, water
  10. dry with materialdried over MgSO4
  11. customevaporated
  12. customThe residue was recrystallized from hexane —Et2O (ca. 10:1)

Sources & evidence

ORD record
ord-66e43f6eecfd4e12a6b50bbef510468c
Source dataset
uspto-grants-2010_09
Patent number
US07803887B2

Reaction notes

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