Piperonal → Bis(1,3-benzodioxol-5-yl)methanol

HRID 339645Notes

Reaction equation

HRID 339645 reaction equation
[CH:1]1[C:6]([CH:7]=[O:8])=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[CH2:12]1[O:20][C:19]2[C:14](=[CH:15][CH:16]=[C-:17][CH:18]=2)[O:13]1.[Mg+2].[Br-]>ClCCl>[CH2:10]1[O:11][C:3]2[CH:2]=[CH:1][C:6]([CH:7]([C:17]3[CH:16]=[CH:15][C:14]4[O:13][CH2:12][O:20][C:19]=4[CH:18]=3)[OH:8])=[CH:5][C:4]=2[O:9]1

Participants

4

Reactant 2

HCID 8438PiperonalHCID 44296443,4-(Methylenedioxy)phenylmagnesium bromide solution

Product 1

HCID 384225Bis(1,3-benzodioxol-5-yl)methanolYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperonal (0.75 g) in solution in dichloromethane (25 ml) was added dropwise 3,4-(methylenedioxy)phenylmagnesium bromide (5 ml, 1M solution in toluene/THF). The mixture was stirred at room temperature overnight, then poured onto water, extracted with dichloromethane, dried and evaporated in vacuo to give the crude alcohol as a brown gum. Purification by column chromatography over silica gel eluting with ethyl acetate in CH2Cl2 (10 to 20%) gave the pure alcohol as a white gum (1.18 g, 87%).

Workup

  1. additionpoured onto water
  2. extractionextracted with dichloromethane
  3. customdried
  4. customevaporated in vacuo
  5. customto give the crude alcohol as a brown gum
  6. customPurification by column chromatography over silica gel eluting with ethyl acetate in CH2Cl2 (10 to 20%)

Sources & evidence

ORD record
ord-8dc9b42c97bd493b9285315c4c2ac31e
Source dataset
uspto-grants-2014_11
Patent number
US08895554B2

Reaction notes

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