4-Hydroxybiphenyl → Ethyl 4-[([1,1'-biphenyl]-4-yl)oxy]butanoate

HRID 1377901Notes

Reaction equation

HRID 1377901 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:20]([O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26]Br)[CH3:21]>CN(C=O)C.C(OCC)C>[CH2:20]([O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:12][CH:11]=1)[CH3:21]

Participants

6

Reactant 3

HCID 71034-HydroxybiphenylHCID 10796Cesium carbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 54135941Ethyl 4-[([1,1'-biphenyl]-4-yl)oxy]butanoateYield 125.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension in dry DMF of 4-phenylphenol (4.99 g,.29.4 mmol) and cesium carbonate (14.35 g, 44.0 mmol) was added ethyl-4-bromobutyrate (8.85 g, 45.3 mmol) in a single portion and the reaction mixture was stirred for 18 hours at ambient temperature. The reaction mixture was diluted with ethyl ether and extracted with pH 7 buffer. The organic phase was washed twice with brine, dried over MgSO4, filtered, and concentrated in vacuo to give 4-(4-phenylphenoxy)butanoic acid ethyl ester (10.48 g) as a white solid.

Workup

  1. extractionextracted with pH 7 buffer
  2. washThe organic phase was washed twice with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41d6a49c86624d28a68a5ce7d3db63bd
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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