Allyl bromide → 5-(Allyloxy)-1,3-benzodioxole-4-carbaldehyde

HRID 42685Notes

Reaction equation

HRID 42685 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[CH:11]=[O:12].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CN(C)C=O>[CH2:21]([O:1][C:2]1[CH:10]=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[C:3]=1[CH:11]=[O:12])[CH:20]=[CH2:19]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 183159245-Hydroxy-1,3-benzodioxole-4-carbaldehyde

Product 1

HCID 112986835-(Allyloxy)-1,3-benzodioxole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-hydroxy-1,3-benzodioxole-4-carbaldehyde (0.166 g, 1.00 mmol) and K2CO3 (1.00 mmol) in dry N,N-dimethylformamide (2 ml) was added allylbromide (1.00 mmol) under argon. The mixture was stirred at room temperature for 18 h until the starting material was consumed (monitored by TLC). Then the mixture was poured onto ice-water (15 ml). The aqueous phase was filtered off, the precipitated product was washed with water and n-heptane and dried to give analytically pure crystals.

Workup

  1. customwas consumed (monitored by TLC)
  2. additionThen the mixture was poured onto ice-water (15 ml)
  3. filtrationThe aqueous phase was filtered off
  4. washthe precipitated product was washed with water and n-heptane
  5. customdried
  6. customto give analytically pure crystals

Sources & evidence

ORD record
ord-1fd67f5cf1a4472db44e6034cd678252
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Reaction notes

Loading…