4,4'-Dihydroxybiphenyl → 4'-[(Prop-2-en-1-yl)oxy][1,1'-biphenyl]-4-ol

HRID 1289262Notes

Reaction equation

HRID 1289262 reaction equation
[C:1]1([OH:14])[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[OH-].[K+].[CH2:17](Br)[CH:18]=[CH2:19]>C(O)C>[CH2:19]([O:14][C:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[CH:5][CH:6]=1)[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 71124,4'-DihydroxybiphenylHCID 7841Allyl bromide2×HCID 14797Potassium Hydroxide

Product 1

HCID 148172454'-[(Prop-2-en-1-yl)oxy][1,1'-biphenyl]-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 1 L, three-necked, round bottom flask 4,4'-biphenol (40 g, 215 mmol) and potassium hydroxide (24 g, 430 mmol) were dissolved in 600 mL of absolute ethanol. The solution was warmed and allyl bromide (26 g, 215 mmol) was added. The reaction mixture was heated to reflux overnight, after which additional allyl bromide (13 g, 157 mmol) was added. The reaction mixture was refluxed for an additional 24 hours. The reaction mixture was cooled to room temperature and the solids were filtered. The filtrate was poured into distilled water (4 L) and then acidified with concentrated aqueous HCl. The solid product was filtered off and washed with a large amount of water and then dried. The product was purified by repeated recrystallization from ethanol. Product characterization included: m.p. 168°-170° C., 1H (200 MHz, CDCl3): 7.05 (m, 4H), 6.8 (m, 4H), 6.1 (m, 1H), 4.4 (m, 2H).

Workup

  1. temperatureThe solution was warmed
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux overnight
  4. temperatureThe reaction mixture was refluxed for an additional 24 hours
  5. filtrationthe solids were filtered
  6. additionThe filtrate was poured
  7. distillationinto distilled water (4 L)
  8. filtrationThe solid product was filtered off
  9. washwashed with a large amount of water
  10. customdried
  11. customThe product was purified
  12. customrecrystallization from ethanol

Sources & evidence

ORD record
ord-37139b7ce0784bdd9867ea987259a590
Source dataset
uspto-grants-1998_05
Patent number
US05747604

Reaction notes

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