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Sodium Bicarbonate → 2,3-Dichloro-6-[(oxiran-2-yl)methyl]phenol

HRID 262387
Notes
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Reaction equation

HRID 262387 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 12747880HCID 12747880, compound

Product 1

HCID 131945502,3-Dichloro-6-[(oxiran-2-yl)methyl]phenol

Reagents, catalysts & solvents 1

HCID 6585Peracetic AcidSolvent

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 ten 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

  1. extractionextracted into ether
  2. washwashed with aqueous sodium bicarbonate, water, aqueous ferrous sulfate, water, brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the ether

Sources & evidence

ORD record
ord-c008a6564749433293bb9fb0d1038549
Source dataset
uspto-grants-1979_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04154742

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes