Vanillin → methyl 2-(4-formyl-2-methoxyphenoxy)acetate

HRID 259782Notes

Reaction equation

HRID 259782 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:8]=1[O:9][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 882523methyl 2-(4-formyl-2-methoxyphenoxy)acetateYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Vanillin was alkylated with methyl bromoacetate in DMF in the presence of K2CO3 in the usual way to give a colorless solid (77%). mp 91°-93 ° C. IR(KBr) cm-1 1760, 1682. 1H NMR(300 MHz, CDCl3): 9.86 (s, 1H), 7.44-7.40 (m, 2H), 6.86 (d, 1H, J=8 Hz), 4.79 (s, 2H), 3.95 (s, 3H), 3.80 (s, 3H). Anal. Calc'd for C11H12O5 : C, 58.92; H, 5.41; Found: C, 59.02; H, 5.26.

Sources & evidence

ORD record
ord-d1c5796127f4492195c1c06baf58a6dc
Source dataset
uspto-grants-1996_06
Patent number
US05523302

Reaction notes

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