Salicylaldehyde → 2-(Methoxymethoxy)benzaldehyde

HRID 2189955Notes

Reaction equation

HRID 2189955 reaction equation
C(O[K])(C)(C)C.[OH:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11].Cl[CH2:17][O:18][CH3:19]>CN(C=O)C>[CH3:17][O:18][CH2:19][O:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 7864Chloromethyl Methyl EtherHCID 178418922HCID 178418922, compound

Product 1

HCID 108774852-(Methoxymethoxy)benzaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Procedure

Into a solution of tert-butoxy potassium (30.0 g, 0.27 mol) in DMF (200 mL) was dropped a solution of 2-hydroxybenzaldehyde (30.0 g, 0.25 mol) in DMF (100 mL) at 0° C. followed by stirring at room temperature for 1 hour. After addition of DMF (200 mL) thereto, a solution of chloromethylmethyl ether (21 mL, 0.27 mol) in DMF (200 mL) was dropped thereinto at 0° C. following by stirring at room temperature for 20 hours. The reaction mixture was poured over ice water followed by extracting with diethyl ether. The organic layer was washed with a 10% aqueous sodium hydroxide and a saturated saline solution successively and then dried over anhydrous sodium sulfate. The solvent was evaporated therefrom in vacuo to give the title compound (32.6 g, 80%) as an oily substance.

Workup

  1. customat 0° C.
  2. stirringby stirring at room temperature for 20 hours
  3. extractionby extracting with diethyl ether
  4. washThe organic layer was washed with a 10% aqueous sodium hydroxide
  5. dry with materiala saturated saline solution successively and then dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7e41f3df66114b06b30a65ad8849f5ba
Source dataset
uspto-grants-2012_12
Patent number
US08324261B2

Reaction notes

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