p-Toluenesulfonic acid monohydrate → 7-(3,5-Di-tert-butylphenyl)-2-((1-methylcyclohexyl)methyl)-1H-indene

HRID 1772403Notes

Reaction equation

HRID 1772403 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:13]([C:17]1[CH:18]=[C:19]([C:27]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:28]=2[CH2:29][CH:30]([CH2:37][C:38]2([CH3:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[CH:31]3O)[CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=1)([CH3:16])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[C:13]([C:17]1[CH:18]=[C:19]([C:27]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:28]=2[CH2:29][C:30]([CH2:37][C:38]2([CH3:44])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[CH:31]3)[CH:20]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:22]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 117817929HCID 117817929, compound

Product 1

HCID 1234608477-(3,5-Di-tert-butylphenyl)-2-((1-methylcyclohexyl)methyl)-1H-indeneYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of p-toluenesulfonic acid monohydrate (0.88 g, 4.64 mmol, 0.2 equiv), compound 14 (10.0 g crude, 23.22 mmol, 1.0 equiv) and toluene (200 mL) was refluxed for 1 h. After cooling to room temperature, the mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL). The organic layer dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified on an AnaLogix (65-200 g) column, eluting with heptanes to give compound 15 (7.8 g, 81% yield for 2 steps) as a white solid.

Workup

  1. temperaturewas refluxed for 1 h
  2. washthe mixture was washed sequentially with saturated sodium bicarbonate (100 mL) and saturated brine (100 mL)
  3. dry with materialThe organic layer dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on an AnaLogix (65-200 g) column
  7. washeluting with heptanes

Sources & evidence

ORD record
ord-2c49f5c181e144ecbf9ff433d6d14fa9
Source dataset
uspto-grants-2016_02
Patent number
US09249239B2

Reaction notes

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