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Water → HCID 57772620, compound

HRID 1522722
Notes
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Reaction equation

HRID 1522722 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)=[O:12])=[CH:6][CH:5]=1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([C:30]([C:32]2[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][CH:33]=2)=O)=O)=[CH:24][CH:23]=1.O>C(O)C.ClCCl>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11](=[O:12])[C:13]([C:14]3[CH:15]=[CH:16][C:17]([Br:20])=[CH:18][CH:19]=3)=[C:28]([C:25]3[CH:26]=[CH:27][C:22]([Br:21])=[CH:23][CH:24]=3)[C:30]=2[C:32]2[CH:33]=[CH:34][C:35]([Br:38])=[CH:36][CH:37]=2)=[CH:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 964304,4'-DibromobenzilHCID 12420215Bis(4-bromobenzyl) ketone

Product 1

HCID 57772620HCID 57772620, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702
Ethanol
Solvent
2×
HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of potassium hydroxide (230 mg, 4.1 mmol) in ethanol (5 cm3) was added to a solution of (13) (3.01 g, 8.2 mmol) and 4,4′-dibromobenzil (3.01 g, 8.2 mmol) in ethanol (45 cm3) at 70° C., and the reaction was stirred at 70° C. for 4 hours. Water (200 cm3) and dichloromethane (200 cm3) were added, and the layers were separated. The organic layer was washed with brine (200 cm3) and dried over magnesium sulfate. The solvent was removed to leave a dark purple solid. The crude product was passed through a plug of silica, and then recrystallised from a dichloromethane/ethanol mixture to give (14) as a dark purple crystalline solid (3.87 g, 68%).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine (200 cm3)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed
  5. customto leave a dark purple solid
  6. customrecrystallised from a dichloromethane/ethanol mixture

Sources & evidence

ORD record
ord-e6bd9eb56a2e41f696ed845ac40c4406
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09078330B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes