4-Hydroxybiphenyl → 1-(Biphenyl-4-yloxy)-2,3-epoxypropane

HRID 2192738Notes

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]([CH:16]1[O:18][CH2:17]1)Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:14]([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)[CH:16]1[O:18][CH2:17]1

Participants

Conditions

Temperature: 30 °C

Procedure

4.7 g of p-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 at 30° C. The mixture was heated to 70° C. and stirred for 16 hours. After filtration, the filtrate was freed from low-boiling components in a rotary evaporator. After addition of 2×30 ml of 2-butanone and redistillation, p-phenylphenol glycidyl ether was obtained as a crystalline solid having a melting range of 96-98° C. 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), 7.00 (AA′BB′ system, 2H), 7.30 (t, 1H), 7.40 (t, 1H), 7.55 (m, 4H).

Workup

temperatureThe mixture was heated to 70° C.
filtrationAfter filtration
customthe filtrate was freed from low-boiling components in a rotary evaporator
additionAfter addition of 2×30 ml of 2-butanone and redistillation

Sources & evidence

ORD record: ord-f9605ba3c47e44508dca8c5abaae843e
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329773B2

Reaction notes

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