Sulfuric Acid → 2-[(2,5-Dimethylphenoxy)methyl]benzaldehyde

HRID 2382244Notes

Reaction equation

HRID 2382244 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[CH3:19].S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[CH3:19][C:13]1[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[O:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:3]=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 67069226HCID 67069226, compound

Product 1

HCID 446094212-[(2,5-Dimethylphenoxy)methyl]benzaldehydeYield 97.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

The crude 2-(2,5-dimethylphenoxymethyl)benzaldehyde dimethyl acetal (73.7 g) obtained in Example 9, 22 mL of xylene and 150.0 g of a 35 wt % sulfuric acid aqueous solution were mixed. The resultant mixture was stirred at 60° C. for 2 hours. To this was added 187 mL of xylene, and the resultant mixture was separated at the same temperature. The resultant organic layer was cooled down to room temperature, then, washed with 75.0 g of a 5 wt % sodium hydroxide aqueous solution, then, with 150 mL of water. The resultant organic layer was concentrated under reduced pressure, to give 60.5 g of crude 2-(2,5-dimethylphenoxymethyl)benzaldehyde as yellow solid. Content: 97.1 wt % Yield: 97.1% (based on 2-(2,5-dimethylphenoxymethyl)benzal chloride)

Workup

  1. customthe resultant mixture was separated at the same temperature
  2. washwashed with 75.0 g of a 5 wt % sodium hydroxide aqueous solution
  3. concentrationThe resultant organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-be7d09f3dd5a4a97902753928709b087
Source dataset
uspto-grants-2012_09
Patent number
US08258349B2

Reaction notes

Loading…