Water → HCID 71278808, compound

HRID 1749715Notes

Reaction equation

HRID 1749715 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2]([OH:8])=[CH:3][C:4]([OH:7])=[CH:5][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH2:20][C:21](Cl)=[O:22].O>[N+](C1C=CC=CC=1)([O-])=O>[OH:8][C:2]1[C:1]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5]2[C:21](=[O:22])[CH2:20][O:7][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 110195784-Phenyl-1,3-Dihydroxybenzene

Product 1

HCID 71278808HCID 71278808, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of biphenyl-2,4-diol (0.24 g, 1.3 mmol) in nitrobenzene (1.0 mL) was added with aluminum chloride (0.60 g, 4.5 mmol) at room temperature. Then, the reaction mixture was added with chloroacetyl chloride (0.60 g, 1.7 mmol) under ice cooling. The mixture was stirred at 40° C. for 3 hours, and then added with water, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (100:0→90:10)) to obtain 6-hydroxy-5-phenylbenzofuran-3(2H)-one (0.12 g, 42%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (100:0→90:10))

Sources & evidence

ORD record
ord-fe55819480df4fd6b87e7cd47745b97e
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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