Phosphorus oxychloride → 2,5-Dimethoxy-4-methylbenzaldehyde

HRID 258752

Reaction equation

HRID 258752 reaction equation
P(Cl)(Cl)(Cl)=O.CN([CH:14]=[O:15])C1C=CC=CC=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[CH3:26]>O>[CH3:25][O:24][C:21]1[CH:20]=[C:19]([CH3:26])[C:18]([O:17][CH3:16])=[CH:23][C:22]=1[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 905522,5-Dimethoxytoluene

Product 1

HCID 6020192,5-Dimethoxy-4-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 40 ml. phosphorous oxychloride (POCl3) and 45 ml. of N-methylformanilide is allowed to stand at ambient temperature for 50 minutes. There is then added 15.2 g. of 2,5-dimethoxytoluene and the resulting solution is heated on the steam bath for 140 minutes. The extremely dark viscous reaction mixture is added to 2 liters of water, and allowed to stir for several hours to complete the hydrolysis of the reaction intermediates. The solid product is removed by filtration, and after washing with water and air-drying yields 16.6 g of reddish crumbly crystals. This solid product is extracted with 2×125 ml. of boiling hexane, which on cooling deposits 12.1 g. of pale cream-colored crystals. Recrystallization from boiling hexane, yields a brilliant white product 2,5-dimethoxy-4-methylbenzaldehyde.

Workup

  1. additionThere is then added 15.2 g
  2. customthe hydrolysis of the reaction intermediates
  3. customThe solid product is removed by filtration
  4. washafter washing with water
  5. customair-drying
  6. customyields 16.6 g of reddish crumbly crystals
  7. extractionThis solid product is extracted with 2×125 ml
  8. temperatureof boiling hexane, which on cooling deposits 12.1 g
  9. customRecrystallization

Sources & evidence

ORD record
ord-8e6229c729fc4ea291324d0404ab2bb4
Source dataset
uspto-grants-1977_07
Patent number
US04034113

Linked notes

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