Sodium borohydride → Methyl (2-hydroxymethyl-5-methylphenoxy)acetate

HRID 482419

Reaction equation

HRID 482419 reaction equation
[CH:1]([C:3]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:4]=1[O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:2].[BH4-].[Na+]>CO.C[O-].[Na+]>[OH:2][CH2:1][C:3]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:4]=1[O:5][CH2:6][C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 54288233Methyl (2-formyl-5-methylphenoxy)acetate

Product 1

HCID 54364037Methyl (2-hydroxymethyl-5-methylphenoxy)acetateYield 82.9%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent

Procedure

By the method of Example 1, Step G, 11.27 g (0.054 mole) of methyl (2-formyl-5-methylphenoxy)acetate was reacted with 0.54 g (0.014 mole) of sodium borohydride and 0.10 g (0.0018 mole) of sodium methoxide in 30 mL of methanol, yielding 9.41 g of methyl (2-hydroxymethyl-5-methylphenoxy)-acetate as a yellow oil. The NMR spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-e37de4ebdd6549958563c391f485231f
Source dataset
uspto-grants-1998_08
Patent number
US05798316

Linked notes

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