Epichlorohydrin → ((o-Allylphenoxy)methyl)oxirane
Reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[CH2:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[CH:7]=[CH2:8].[OH-].[Na+]>C(C1C=CC=CC=1O)C=C.O>[CH2:1]([O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:6][CH:7]=[CH2:8])[CH:3]1[O:5][CH2:4]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
This allyl phenyl ether was introduced into an autoclave and held at 200° C. for 5 hours with stirring. In this stage, a rearrangement reaction occurred to obtain 2-allylphenol. Into a reaction vessel, 134 g (1 mol) of the 2-allylphenol and 1.3 g of a boron trifluoride ether complex as a catalyst were introduced. In a nitrogen atmosphere, the contents were heated to 100° C. with stirring, and epichlorohydrin was added dropwise thereto in an amount of 1 mol per mole of the 2-allylphenol, with stirring the contents and maintaining that temperature. Thereafter, 100 g of 48% aqueous sodium hydroxide solution was added dropwise thereto at 60° C., and the resultant mixture was aged at 60° C. for 2 hours. Subsequently, 400 g of water was added thereto, and this mixture was stirred at 80° C. for 30 minutes and then allowed to stand still at 80° C. for 1 hour. The lower layer (aqueous layer) which had separated was removed, followed by dehydration at 100° C. under vacuum to obtain 2-allylphenyl glycidyl ether.
Workup
- temperaturemaintaining that temperature
- stirringthis mixture was stirred at 80° C. for 30 minutes
- customThe lower layer (aqueous layer) which had separated
- customwas removed
- customfollowed by dehydration at 100° C. under vacuum
Sources & evidence
- ORD record
- ord-0202b8de503d45f695134b6074fc3358
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376510B2
Reaction notes
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