Vanillin → 3-Methoxy-4-(methoxymethoxy)benzaldehyde

HRID 714148

Reaction equation

HRID 714148 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][CH2:20]Cl>CN(C)C=O>[CH3:18][O:19][CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 1183VanillinHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium Carbonate

Product 1

HCID 796613-Methoxy-4-(methoxymethoxy)benzaldehydeYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-3-methoxybenzaldehyde (1a, 2.00 g, 13.1 mmol) and potassium carbonate (9.00 g, 65.1 mmol) were combined in dimethyl formamide (30 ml) and stirred for 15 min at room temperature. Chloromethyl methyl ether (1.60 ml, 21.1 mmol) was added and stirring was continued for 6 hr at room temperature. The resulting mixture was filtered and the filtrate extracted into ethyl acetate, washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to give 2.55 g (99%) of a white solid: mp 39-40° C. [expected mp 41° C.]; 1H NMR: δ 3.40 (s, 3H), 3.83 (s, 3H), 5.21 (s, 2H), 7.15 (d, 1H, J=8.7 Hz), 7.30 (dd, 1H, J=6.0, 2.0 Hz), 7.32 (s, 1H), 9.75 (s, 1H); 13C NMR: δ 55.8, 56.2, 94.8, 109.4, 114.6, 125.9, 130.9, 149.8, 151.7, 190.4.

Workup

  1. stirringstirring
  2. waitwas continued for 6 hr at room temperature
  3. filtrationThe resulting mixture was filtered
  4. extractionthe filtrate extracted into ethyl acetate
  5. washwashed with saturated sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-94d696110c384bc9991574215c3ef340
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Linked notes

Loading…