Dimethylformamide → HCID 13066662, compound

HRID 1163985Notes

Reaction equation

HRID 1163985 reaction equation
[OH:1][C:2]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].S(OC)(O[CH3:22])(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:22][O:1][C:2]1[C:9]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 13066661HCID 13066661, compound

Product 1

HCID 13066662HCID 13066662, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Hydroxy-3-(o-tolyloxy)benzaldehyde (64.20 g), dimethyl sulfate (46.10 g) and powdered potassium carbonate (50.50 g) were added to dimethylformamide (150 ml) and stirred at room temperature for 2 hrs. The reaction mixture was poured into water (1 l), and the precipitating crystals were collected by filtration. The aqueous filtrate was extracted with diethyl ether, and the crystals obtained above were dissolved in the extract. The ether solution was washed with water, dried over magnesium sulfate and evaporated. The crystalline residue was recrystallized from methanol to give colorless crystals of 2-methoxy-3-(o-tolyloxy)benzaldehyde (48.70 g). mp 53°-55° C.

Workup

  1. filtrationthe precipitating crystals were collected by filtration
  2. extractionThe aqueous filtrate was extracted with diethyl ether
  3. customthe crystals obtained
  4. dissolutionabove were dissolved in the extract
  5. washThe ether solution was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe crystalline residue was recrystallized from methanol

Sources & evidence

ORD record
ord-bded21b0512b4c86b7d254a04150bde3
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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