2-Bromo-1,2-diphenylethan-1-one → 2-Oxo-1,2-diphenylethyl 3'-hydroxy-3-biphenylcarboxylate

HRID 377318

Reaction equation

HRID 377318 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[C:18]1([C:24]([CH:26](Br)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C.S(=O)(=O)(O)O>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([O:17][CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:24](=[O:25])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 1026302-Bromo-1,2-diphenylethan-1-oneHCID 27593013'-Hydroxy-[1,1'-biphenyl]-3-carboxylic acidHCID 5360545Sodium

Product 1

HCID 193584852-Oxo-1,2-diphenylethyl 3'-hydroxy-3-biphenylcarboxylateYield 78.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 702EthanolSolvent

Procedure

Sodium (64 mg) was dissolved in ethanol (10 ml) and 3'-hydroxy-3-biphenylcarboxylic acid (0.5 g) was added thereto. The mixture was stirred at room temperature for 20 minutes, and then conc. sulfuric acid (1 drop) and desyl bromide (642 mg) was added thereto. The resulting mixture was stirred under reflux for 3 hours, cooled to room temperature, and partitioned between water and ethyl acetate. The organic layer was washed successively with water (twice), 1N hydrochloric acid, sodium bicarbonate aqueous solution, and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed (n-hexane--ethyl acetate) over silica gel to afford 2-oxo-1,2-diphenylethyl 3'-hydroxy-3-biphenylcarboxylate (744 mg) as a paste.

Workup

  1. stirringThe resulting mixture was stirred
  2. temperatureunder reflux for 3 hours
  3. temperaturecooled to room temperature
  4. custompartitioned between water and ethyl acetate
  5. washThe organic layer was washed successively with water (twice), 1N hydrochloric acid, sodium bicarbonate aqueous solution, and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed (n-hexane--ethyl acetate) over silica gel

Sources & evidence

ORD record
ord-5f59ee9d9abf416fa531218a877a7115
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Linked notes

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