Benzyl Bromide → 1-Benzyloxy-2,3-methylenedioxybenzene

HRID 1904957Notes

Reaction equation

HRID 1904957 reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([OH:10])[CH:5]=[CH:6][CH:7]=2)[O:2]1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:11]([O:10][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]=12)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5867271,3-Benzodioxol-4-ol

Product 1

HCID 141805661-Benzyloxy-2,3-methylenedioxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2,3-methylenedioxyphenol (17.45g) and benzyl bromide (27.5 mL) in dimethylformamide (200 ml) was treated with potassium carbonate (35 g), and the mixture was heated at 60° C. overnight. After cooling and filtering, the mixture was evaporated. The residue was dissolved in ethyl acetate and washed with 1 M hydrochloric acid. The organic extract was dried, filtered and evaporated to afford 1-benzyloxy-2,3-methylenedioxybenzene, mp 62°-63° C.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltering
  3. customthe mixture was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1 M hydrochloric acid
  6. extractionThe organic extract
  7. customwas dried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-e639a2c420b2498c819b3365ad8464a7
Source dataset
uspto-grants-1989_06
Patent number
US04840965

Reaction notes

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