Ethyl Acetate → Ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylate

HRID 1603897Notes

Reaction equation

HRID 1603897 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(OCC)(=O)C>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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 12252872Ethyl 3-allyl-4-hydroxybenzoate

Product 1

HCID 13728720Ethyl 2-hydroxymethyl-2,3-dihydrobenzofuran-5-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of ethyl 3-allyl-4-hydroxybenzoate (6.74 g, 32.7 mmol) in chloroform (105 ml) was added with meta-chloroperbenzoic acid (11.40 g, 66.1 mmol) and the mixture was refluxed under stirring for 4 h. Afterwards, the solvent was evaporated, the crude was redissolved in ethyl acetate and washed with a 1M NaOH solution. After drying and removing the solvent, a crude was obtained which was purified by chromatography through a silica gel column, eluting with n-hexane:ethyl acetate, 90:10, to recover 5.95 g of the title compound (82% yield).

Workup

  1. temperaturethe mixture was refluxed
  2. customAfterwards, the solvent was evaporated
  3. dissolutionthe crude was redissolved in ethyl acetate
  4. washwashed with a 1M NaOH solution
  5. customAfter drying
  6. customremoving the solvent
  7. customa crude was obtained which
  8. customwas purified by chromatography through a silica gel column
  9. washeluting with n-hexane

Sources & evidence

ORD record
ord-83eeded8d2be44718469228baee805e9
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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