Phenol → 1-Phenoxy-2,3-epoxybutane

HRID 580690Notes

Reaction equation

HRID 580690 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][CH:10]1[O:13][CH:11]1[CH3:12].Br[CH:15]([CH3:19])[CH:16]1[O:18][CH2:17]1>>[O:7]([CH:15]([CH3:19])[CH:16]1[O:18][CH2:17]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:7]([CH2:12][CH:11]1[O:13][CH:10]1[CH3:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 122111012-(1-Bromoethyl)oxiraneHCID 127416282-(Bromomethyl)-3-methyloxirane

Product 2

HCID 201345631-Phenoxy-2,3-epoxybutaneHCID 224653483-Phenoxy-1,2-epoxybutane

Procedure

Rowton et al., J. Org. Chem. 23 1057 (1958) discloses the reaction of phenol with 1-bromo-2,3-epoxybutane and 3-bromo-1,2-epoxybutane to yield 3-phenoxy-1,2-epoxybutane and 1-phenoxy-2,3-epoxybutane, respectively.

Sources & evidence

ORD record
ord-2f45d4521d2948a8820ace0349d9b597
Source dataset
uspto-grants-1988_06
Patent number
US04754076

Reaction notes

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