Ethyl bromoacetate → 40359-30-6

HRID 1900219Notes

Reaction equation

HRID 1900219 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:13][C:14]([O:16]CC)=[O:15]>C(#N)C>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([O:10][CH3:11])[C:2]=1[O:1][CH2:13][C:14]([OH:16])=[O:15])=[O:5]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 8991o-Vanillin2×

Product 1

HCID 73758940359-30-6

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The starting product is 2-hydroxy-3-methoxy benzaldehyde, known commonly as o-vanillin. Alkylation is conducted by the already described method, using ethyl bromoacetate under reflux in acetonitrile. In this manner 2-formyl-6-methoxy-phenoxyacetic acid is obtained in the form of the ethyl ester. The oily crude product is saponified to give the corresponding acid in the form of a white crystalline solid. Melting point 118/119° C. NMR (DMSO-d6): 13 (b, 1H), 10.5 (s, 1H), 7.4/7.1 (m, 3H), 4.8 (s, 2H), 3.85 (s, 3H). IR (KBr, cm-1): 3100/2600, 1735, 1700. This is transformed into the corresponding oxime using hydroxylamine hydrochloride.

Sources & evidence

ORD record
ord-8fd06235a53f42efaadd8b558ec31c85
Source dataset
uspto-grants-1996_11
Patent number
US05574153

Reaction notes

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