Sodium borohydride → Methyl 2-(3-hydroxymethylphenoxy)propionate

HRID 257391Notes

Reaction equation

HRID 257391 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[O:2].[BH4-].[Na+]>CO.C[O-].[Na+]>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][CH:15]=1)[O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18759681Methyl 2-(3-formylphenoxy)propanoate

Product 1

HCID 18759680Methyl 2-(3-hydroxymethylphenoxy)propionateYield 97.5%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent

Procedure

By the method of Example 1, Step I, 15.7 g (0.0761 mole) of methyl 2-(3-formylphenoxy)propionate, 0.76 g (0.020 mole) of sodium borohydride, and 0.10 g (0.0018 mole) of sodium methoxide were reacted in 40 mL of methanol, yielding 15.6 g of methyl 2-(3-hydroxymethylphenoxy)propionate as a yellow liquid. The NMR and IR spectra were consistent with the proposed structure.

Sources & evidence

ORD record
ord-27b68504aada4bfc9d4e7da74b69559a
Source dataset
uspto-grants-1993_11
Patent number
US05262390

Reaction notes

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