Hydrochloric Acid → 4,5-Dimethoxy-2-methylbenzaldehyde

HRID 1587719Notes

Reaction equation

HRID 1587719 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:11])C=[CH:7][C:8]=1[O:9][CH3:10].ClC([O:15]C)Cl.Cl[Sn](Cl)(Cl)Cl.Cl[CH:23](Cl)[CH3:24].Cl>ClCCl>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([CH:11]=[O:15])=[C:23]([CH3:24])[CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 63651,1-DichloroethaneHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 681263,4-Dimethoxytoluene

Product 1

HCID 821414,5-Dimethoxy-2-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,4-dimethoxytoluene (15 g) and dichloromethylmethyl ether (34.5 g) in dichloromethane (200 ml), at 0° C., was added SnCl4 (100 ml) and, subsequently, further dichloroethane (200 ml). The resultant suspension was stirred at 0° C. for 20 minutes and then stirred overnight at ambient temperature before being poured into 3N HCl (500 ml) at 0° C. Extraction into dichloromethane, drying of the organic phase and evaporation gave 4,5-dimethoxy-2-methylbenzaldehyde (15.2 g); NMR (CDCl3) 2.6(s,3H); 3.90(s,3H); 3.94(s,3H); 6.68(s,1H); 7.3(s,1H); 10.2(s,1H).

Workup

  1. extractionExtraction into dichloromethane
  2. customdrying of the organic phase and evaporation

Sources & evidence

ORD record
ord-2f6792319cc84ade97522ae5166bd6f6
Source dataset
uspto-grants-1993_06
Patent number
US05219848

Reaction notes

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