3,4-Dichlorobenzyl chloride → 4-(3,4-Dichlorobenzyloxy)-3-methylbenzaldehyde

HRID 558166Notes

Reaction equation

HRID 558166 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([Cl:10])[CH:4]=1.[OH:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][C:13]=1[CH3:20].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:10][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[Cl:9])[CH2:2][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][C:13]=1[CH3:20]

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 11430Potassium CarbonateHCID 1399014-Hydroxy-3-methylbenzaldehyde

Product 1

HCID 230733414-(3,4-Dichlorobenzyloxy)-3-methylbenzaldehydeYield 99.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.5M solution of 4-chloromethyl-1,2-dichloro-benzene (1.55 g, 8.0 mmol) in DMF was added dropwise to a suspension of 4-hydroxy-3-methyl-benzaldehyde (990 mg, 7.3 mmol), K2CO3 (1.51 g, 11 mmol) and KI (120 mg, 0.73 mmol) in DMF (100 ml). The reaction mixture was treated as described in Example 6. The residue was purified on silica gel, obtaining 2.15 g of the title compound in a quantitative yield.

Workup

  1. additionThe reaction mixture was treated
  2. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-ceb9bf25bb54464b82e1e54f2003aab6
Source dataset
uspto-grants-2011_11
Patent number
US08063039B2

Reaction notes

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