4-Hydroxybenzaldehyde → Methyl 2-(4-formylphenoxy)propanoate

HRID 257394Notes

Reaction equation

HRID 257394 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.Br[CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:11]([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:3][CH:4]=1)=[O:7]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionate

Product 1

HCID 18981016Methyl 2-(4-formylphenoxy)propanoateYield 71.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By the method of Example 1, Step H, 10.0 g (0.0819 mole) of 4-hydroxybenzaldehyde and 16.4 g (0.0983 mole) of methyl 2-bromopropionate were reacted in the presence of 13.6 g (0.0983 mole) of anhydrous potassium carbonate in N,N-dimethylformamide, yielding 12.2 g of methyl 2-(4-formylphenoxy)propionate as a yellow liquid. The NMR and IR spectra were consistent with the proposed structure.

Sources & evidence

ORD record
ord-bf497e0df45d4f299cfb4b676c60d424
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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