Sodium Iodide → Methyl 3-(2-formyl-3-methoxyphenoxy)methylbenzoate

HRID 647918Notes

Reaction equation

HRID 647918 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=[O:5].Br[CH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CO>[CH:4]([C:3]1[C:6]([O:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][CH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])=[O:5]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 696926-MethoxysalicylaldehydeHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 20484350Methyl 3-(2-formyl-3-methoxyphenoxy)methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Hydroxy-6-methoxybenzaldehyde (4.56 g, 0.03 M), methyl 3-bromomethylbenzoate (6.87 g, 0.03 M), anhydrous potassium carbonate (4.455 g), sodium iodide (0.18 g) and methanol (50 ml) were refluxed with stirring for 18 hr. The cooled reaction mixture was filtered and the solid washed well with methanol. The filtrate was evaporated to dryness and the residue triturated with 1 N sodium hydroxide solution. The solid was filtered off and washed with water to give methyl 3-(2-formyl-3-methoxyphenoxy)methylbenzoate, 3.27 g, 36%, m.p. 96°-97° C. from ethyl acetate/petrol.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. washthe solid washed well with methanol
  4. customThe filtrate was evaporated to dryness
  5. customthe residue triturated with 1 N sodium hydroxide solution
  6. filtrationThe solid was filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-937f9f6412964a73b7c7fa06b7c8aa77
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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