3-Phenylphenol → 2-{[([1,1'-Biphenyl]-3-yl)oxy]methyl}oxirane

HRID 2192739Notes

Reaction equation

HRID 2192739 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:14]([O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=1)[CH:16]1[O:18][CH2:17]1

Participants

5

Reactant 3

HCID 113813-PhenylphenolHCID 11430Potassium CarbonateHCID 18430Epibromohydrin

Product 1

HCID 147968222-{[([1,1'-Biphenyl]-3-yl)oxy]methyl}oxirane

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4.7 g of m-phenylphenol, 15.1 g of epibromohydrin, 13.6 g of potassium carbonate and 33.3 g of 2-butanone were introduced into a three-necked flask with reflux condenser and stirrer. In addition, air was slowly passed through and the temperature was held at 70° C., and the mixture was stirred for 15 hours. After filtration, the filtrate was freed from low-boiling components in a rotary evaporator. m-Phenylphenol glycidyl ether was obtained as a clear, liquid product: 1H-NMR (CDCl3, 400 MHz): 2.78 (dd, 1H), 2.90 (t, 1H), 3.36 (m, 1H), 4.02 (dd, 1H), 4.24 (dd, 1H), 6.90 (dd, 1H), 7.15 (d, 1H), 7.20 (d, 1H), 7.35 (m, 2H), 7.40 (t, 2H), 7.55 (d, 2H).

Workup

  1. temperaturewith reflux condenser and stirrer
  2. customwas held at 70° C.
  3. filtrationAfter filtration
  4. customthe filtrate was freed from low-boiling components in a rotary evaporator

Sources & evidence

ORD record
ord-a0165680b1834be0b587e28f453c51d6
Source dataset
uspto-grants-2012_12
Patent number
US08329773B2

Reaction notes

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