Guaiacol → ((o-Methoxyphenoxy)methyl)oxirane
Reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].CC(C)([O-])C.[K+].[CH2:16]([CH:18]1[O:20][CH2:19]1)Cl.C1OCCOCCOCCOCCOCCOC1>C(O)(C)(C)C.O>[O:20]1[CH2:19][CH:18]1[CH2:16][O:3][C:2]1[CH:4]=[CH:5][CH:6]=[CH:7][C:1]=1[O:8][CH3:9]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
Guaiacol (8.6 g, 69 mmol), potassium t-butoxide (7.8 g, 69 mmol), epichlorohydrin (19.3 g, 209 mmol), and 18-crown-6 (0.8 g) were mixed in t-butanol (100 ml) and heated to 50° C. for 2 h. Water was added and the product was extracted with two portions of dichlorometane. Washing with water, twice, was followed by drying and evaporation. Quantitative yield.
Workup
- extractionthe product was extracted with two portions of dichlorometane
- washWashing with water
- customby drying
- customevaporation
Sources & evidence
- ORD record
- ord-7f06efcd61404ef7987c209d8f77713a
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479491B1
Reaction notes
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