Dibromomethane → 1,3-Benzodioxole-4-carboxaldehyde

HRID 1980798Notes

Reaction equation

HRID 1980798 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[OH-].[Na+].[CH2:13](Br)Br>O>[CH2:13]1[O:10][C:9]2[C:2](=[C:3]([CH:6]=[CH:7][CH:8]=2)[CH:4]=[O:5])[O:1]1

Participants

5

Reactant 3

HCID 3024DibromomethaneHCID 14798Sodium HydroxideHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 822641,3-Benzodioxole-4-carboxaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(a) A mixture of 2,3-dihydroxybenzaldehyde (6.4 g, 50 mmol) and sodium hydroxide (5 g in 25 ml of water) was added over 110 mins to a refluxing mixture of methylene bromide (17.3 g, 100 mmol), N,N,N-[tri-(C8 to C10 alkyl)]-N-methylammonium chloride (0.5 g; supplied by Aldrich Chemicals under the Trade Name "Adogen" 464) and water (10 ml). The mixture was heated at reflux for a further 5 hr under nitrogen and then steam distilled. The distillate was extracted with dichloromethane. Evaporation of the dried (MgSO4) organic extract gave 2,3-methylenedioxybenzaldehyde (3.2 g, 46%) as a yellow oil. Pmr spectrum (CDCl3 ; δ in ppm): 6.03 (2H,s); 6.66-6.99 (2H,m); 7.02-7.25 (1H,m); 9.97 (1H,s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for a further 5 hr under nitrogen
  3. distillationsteam distilled
  4. extractionThe distillate was extracted with dichloromethane
  5. customEvaporation of the
  6. dry with materialdried (MgSO4)
  7. extractionorganic extract

Sources & evidence

ORD record
ord-e39f0c9eff3c476ab08041bcb7bd75d5
Source dataset
uspto-grants-1985_04
Patent number
US04511391

Reaction notes

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