Catechol → 2-[(2-methyl-2-propenyl)oxy]phenol
Reaction equation
[CH2:1](Cl)[C:2](=[CH2:4])[CH3:3].[C:6]1([C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9])[OH:7]>>[CH2:1]([O:7][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=1[OH:9])[C:2](=[CH2:4])[CH3:3]Participants
Procedure
These Examples A-D show that if the alkaline reagent used is sodium hydroxide or potassium hydroxide, an increase in the amount of methallyl chloride used improves the degree of conversion of the pyrocatechol as well as the yield of monoether, but results in a substantial formation of diether and of benzene ring alkylation products. Thus, if reference is made to Examples B and D, the use of one mol of methallyl chloride per mol of pyrocatechol, results in monoether/diether molar ratios of, respectively, 1.8 in Example B and 3.8 in Example D. If reference is now made to Examples 1 to 14 according to the present Patent Application, it will be seen that according to the process claimed, it is possible to use large amounts of methallyl chloride without reducing the selectivity of the reaction. Thus, according to Example 1, the use of 1.5 mols of methallyl chloride per mol of pyrocatechol makes it possible to achieve a molar ratio of monoether/diether of 7.6, whilst having a yield of 68% of o-methallyloxyphenol relative to the pyrocatechol starting material, and a content of benzene nucleus alkylation products of 4% relative to pyrocatechol converted.
Workup
- customthe selectivity of the reaction
Sources & evidence
- ORD record
- ord-dbfda025b53c4d79943d843d49f06a26
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04250333
Reaction notes
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