4-Hydroxybiphenyl → HCID 18799544, compound

HRID 1637648Notes

Reaction equation

HRID 1637648 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]2[CH:10]=[C:11](C=CC(O)=O)[CH:12]=[CH:13][CH:14]=2)=[CH:3][CH:2]=1.C1(C2C=CC(O)=CC=2)C=CC=CC=1.[H-].[Na+].[Br:41]C1C=C(C=CC=1)CBr>CN(C)C=O.O>[Br:41][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH2:8][O:7][C:4]1[CH:5]=[CH:6][C:1]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 71034-HydroxybiphenylHCID 24758Sodium hydrideHCID 699793-Bromobenzyl bromideHCID 54389811HCID 54389811, compound

Product 1

HCID 18799544HCID 18799544, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(3-(Biphenyl-4-yloxymethyl)phenyl)acrylic acid ##STR3## To a solution of 4-phenylphenol (6.13 g, 36 mmol) in dry N,N-dimethyl-formamide (100 ml) kept under an atmosphere of nitrogen, sodium hydride (1.73 g, 43.2 mmol, 60% dispersion in mineral oil) was added in portions and the reaction mixture was stirred until gas evolution ceased. 3-Bromobenzyl bromide (10.0 g, 39.61 mmol) was added in portions and the reaction mixture was stirred at room temperature for 18 h. To the reaction mixture water (50 ml) was added. The precipitate was filtered off and washed with water (3×100 ml), 96% ethanol (2×30 ml), diethyl ether (2×80 ml), and dried in vacuo at 50° C. for 18 h affording 11.64 g (95 %) of 4-(3-bromo-benzyloxy)biphenyl as a solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 h
  2. filtrationThe precipitate was filtered off
  3. washwashed with water (3×100 ml), 96% ethanol (2×30 ml), diethyl ether (2×80 ml)
  4. customdried in vacuo at 50° C. for 18 h

Sources & evidence

ORD record
ord-7db5e143f607439b87aac21ec84a746f
Source dataset
uspto-grants-2000_03
Patent number
US06043247

Reaction notes

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