Acetic Acid → HCID 15161005, compound

HRID 1535059Notes

Reaction equation

HRID 1535059 reaction equation
[CH2:1]([C:4]1[C:16]([OH:17])=[CH:15][C:7]2[C:8]([CH3:14])([CH3:13])[CH:9]([O:11]C)[O:10][C:6]=2[CH:5]=1)[CH:2]=[CH2:3].C(O)(=O)C>O>[CH2:1]([C:4]1[C:16]([OH:17])=[CH:15][C:7]2[C:8]([CH3:13])([CH3:14])[CH:9]([OH:11])[O:10][C:6]=2[CH:5]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 15161003HCID 15161003, compound

Product 1

HCID 15161005HCID 15161005, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-allyl-3,3-dimethyl-5-hydroxy-2-methoxy-2,3-dihydrobenzofuran, E70a, (20 gm; 85 mmoles), acetic acid (160 mL) and water (40 mL) was refluxed for 18 hours. The mixture was concentrated in vacuo and the residue chromatographed on silica gel using 20% ethyl acetate in hexane as eluent to obtain 17.8 gm (94%) of 6-allyl-2,5-dihydroxy-3,3-dimethyl-2,3-dihydrobenzofuran, E79, m.p. 66°-67° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue chromatographed on silica gel using 20% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-39899ddcd3774c16a26d1cfefd0d7409
Source dataset
uspto-grants-1992_02
Patent number
US05091533

Reaction notes

Loading…