m-Chloroperbenzoic acid → Ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylate

HRID 256399Notes

Reaction equation

HRID 256399 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][C:14]=1[OH:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:24])C=1>C(Cl)(Cl)Cl>[OH:24][CH2:3][CH:2]1[CH2:1][C:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:12]=[CH:13][C:14]=2[O:15]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12252872Ethyl 3-allyl-4-hydroxybenzoate

Product 1

HCID 13728720Ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylateYield 63.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 47.1 g (0.228 mole) ethyl 3-allyl4-hydroxybenzoate, 350 ml chloroform and 79.7 g (0.462 mole) m-chloroperbenzoic acid was heated at reflux, with stirring, under nitrogen for 3.5 hours. The resulting mixture was allowed to cool to room temperature, the solvent evaporated, the residue dissolved in ethyl ether, washed with 1N sodium hydroxide, brine and dried (MgSO4). Evaporation of the ether gave 32.07 g of product as a colorless solid, m.p. 72°-77° C. which was used in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customthe solvent evaporated
  4. dissolutionthe residue dissolved in ethyl ether
  5. washwashed with 1N sodium hydroxide, brine
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the ether

Sources & evidence

ORD record
ord-824a5b5fbbb04697816c18f08f1c39b7
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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