4-Hydroxybiphenyl → HCID 59595831, compound

HRID 2264535Notes

Reaction equation

HRID 2264535 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.[CH2:14]([O:16][CH:17]([O:20][CH2:21][CH3:22])[CH2:18]Br)[CH3:15].[OH-].[K+]>CS(C)=O.O>[CH2:14]([O:16][CH:17]([O:20][CH2:21][CH3:22])[CH2:18][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)[CH3:15]

Participants

6

Reactant 3

HCID 71034-HydroxybiphenylHCID 14797Potassium Hydroxide2×HCID 74852Ethane, 2-bromo-1,1-diethoxy-

Product 1

HCID 59595831HCID 59595831, compoundYield 94.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 4-phenylphenol (5 g, 29.4 mmol), bromoacetaldehyde diethyl acetal (4.56 mL, 29.4 mmol) and KOH (1.94 g, 29.4 mmol) in DMSO (15 mL) was stirred at reflux for 6 h. The reaction mixture was allowed to cool down to room temperature and poured over ice containing 0.60 g of KOH and diluted to 100 mL with water. The solution was extracted with Et2O (20 mL×3); the combined extracts were washed with 1N NaOH solution, water and brine, dried, and concentrated under reduced pressure to yield 7.97 g (94%) of a yellow oil that was used without further purification: 1H NMR (400 MHz, CDCl3) δ 7.56-7.50 (m, 4H), 7.41 (t, 2H), 7.30 (t, 1H), 7.00 (dt, 2H), 4.86 (t, 1H), 4.05 (d, 2H), 3.82-3.74 (m, 2H), 3.69-3.62 (m, 2H).

Workup

  1. temperatureat reflux for 6 h
  2. extractionThe solution was extracted with Et2O (20 mL×3)
  3. washthe combined extracts were washed with 1N NaOH solution, water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59c75fdab9c541e396cf48283f384c40
Source dataset
uspto-grants-2010_12
Patent number
US07855193B2

Reaction notes

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