Sodium Bicarbonate → 2,3-Dichloro-6-[(oxiran-2-yl)methyl]phenol
Reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].[Cl:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[C:9]([CH2:14]C=C)[C:8]=1[OH:17].C(=O)(O)[O-].[Na+]>C(OO)(=O)C>[Cl:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[C:9]([CH2:14][CH:1]2[O:4][CH2:2]2)[C:8]=1[OH:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A stirred solution of sodium acetate (1 g.) in 40% peracetic acid (25 ml.) is cooled to 15° C. then treated dropwise with 2,3-dichloro-6-allylphenol. The reaction mixture is stirred at 25° C. for 48 hours, poured into excess aqueous sodium bicarbonate, extracted into ether, washed with aqueous sodium bicarbonate, water, aqueous ferrous sulfate, water, brine and dried over magnesium sulfate. Evaporation of the ether leaves 2,3-dichloro-6-(2,3-epoxypropyl)phenol which is rearranged by heating at 110° C. for 10 minutes then distilled to give 10.4 g. of 6,7-dichloro-2,3-dihydro-2-hydroxymethylbenzofuran which boils at 130°/0.1 mm.
Workup
- extractionextracted into ether
- washwashed with aqueous sodium bicarbonate, water, aqueous ferrous sulfate, water, brine
- dry with materialdried over magnesium sulfate
- customEvaporation of the ether
Sources & evidence
- ORD record
- ord-206549448d8e4a12b9afc49cb0b4a419
- Source dataset
- uspto-grants-1978_05
- Patent number
- US04087542
Reaction notes
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