Water → HCID 22748763, compound

HRID 2389313Notes

Reaction equation

HRID 2389313 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.[NH:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]1=[O:23].OS(O)(=O)=O.O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[C:21]2[CH:20]=[CH:19][C:18](=[O:23])[NH:17][CH:22]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 88712-PyridoneHCID 2793564,4'-Dimethylbenzhydrol

Product 1

HCID 22748763HCID 22748763, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of bis(4-methylphenyl)methanol (5 g), and pyridin-2(1H)-one (6.72 g) was stirred at 180° C. To the solution was added concentrated H2SO4 (0.07 mL), and the mixture was stirred at 250° C. for 2 hours. Water (15 mL) and DCM (15 mL) were poured into the reaction mixture. The organic layer was washed with water and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc). The desired fractions were collected and evaporated in vacuo, and the residue was washed with MeCN and dried in vacuo to give 5-[bis(4-methylphenyl)methyl]pyridin-2(1H)-one (0.94 g) as white crystals.

Workup

  1. stirringthe mixture was stirred at 250° C. for 2 hours
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo
  9. washthe residue was washed with MeCN
  10. customdried in vacuo

Sources & evidence

ORD record
ord-1a295ac675854df794de7d421a926c51
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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