Ethanol → HCID 19936580, compound

HRID 258049Notes

Reaction equation

HRID 258049 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[O:19]C)[CH2:15][CH2:14][CH2:13]2)=[O:9])([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br.ClCCl.C(O)C>ClCCl>[C:25]([C:22]1[CH:21]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:23]=1[OH:24])[C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[OH:19])[CH2:15][CH2:14][CH2:13]2)=[O:9])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 702EthanolHCID 19936579HCID 19936579, compoundHCID 22277759Boron tribromide dichloromethane

Product 1

HCID 19936580HCID 19936580, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3,5-di-tert-butyl-4-hydroxybenzoyl)-6-methoxyindan (3.8 g) in dichloromethane (30 ml) was added boron tribromide-dichloromethane (1:2, 3 ml) dropwise with ice-cooling and stirring. The mixture was stirred under ice-cooling for 15 minutes, after which ethanol (5 ml) was added dropwise. The mixture was then washed with water and dried (MgSO4) and the solvent was distilled off. To the residue was added hexane to give crystals of 5-(3,5-di-tert-butyl-4-hydroxybenzoyl)-6-hydroxyindan (3.06 g, 83.6%). Recrystallization from ethanol gave light yellow prisms, m.p. 155°-156° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred under ice-
  3. temperaturecooling for 15 minutes
  4. washThe mixture was then washed with water
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off
  7. additionTo the residue was added hexane

Sources & evidence

ORD record
ord-82b4175a511f4e1f97ebe9003496ceae
Source dataset
uspto-grants-1993_11
Patent number
US05264454

Reaction notes

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