1,2-Dichlorobenzene → 2-allyl-4,5-(methylenedioxy)phenol

HRID 1600855Notes

Reaction equation

HRID 1600855 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([O:10]CC=C)=[CH:4][C:3]=2[O:2]1.Cl[C:15]1[CH:20]=CC=C[C:16]=1Cl>>[CH2:20]([C:6]1[CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]2=[CH:4][C:5]=1[OH:10])[CH:15]=[CH2:16]

Participants

3

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 5862725-[(Prop-2-en-1-yl)oxy]-2H-1,3-benzodioxole

Product 1

HCID 6012672-allyl-4,5-(methylenedioxy)phenolYield 92%

Procedure

A solution of allyl 3,4-(methylenedioxy)phenyl ether (2.4 g, 13 mmol), was dissolved in 30 ml of 1,2-dichlorobenzene and the solution was refluxed for 18 h. The solvent was removed under high vacuum in a water bath set at 60° C. The remaining oil was extracted into ether, washed with brine and dried over MgSO4. The solvent was removed under vacuum to give a yellow oil which was further purified by flash column chromatography. Elution with 10% ethyl acetate/hexanes gave 2.2 g (92%) of the pure compound as a pale yellow oil.

Workup

  1. temperaturethe solution was refluxed for 18 h
  2. customThe solvent was removed under high vacuum in a water bath
  3. customset at 60° C
  4. extractionThe remaining oil was extracted into ether
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under vacuum
  8. customto give a yellow oil which
  9. customwas further purified by flash column chromatography
  10. washElution with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-74def081d93847078ca4c57beaeb4ebe
Source dataset
uspto-grants-1999_11
Patent number
US05977117

Reaction notes

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