Sodium borohydride → Methyl 2-(4-hydroxymethyl-2-methylphenoxy)phenylacetate

HRID 2255594Notes

Reaction equation

HRID 2255594 reaction equation
[CH:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:5]([CH3:21])[CH:4]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:5]([CH3:21])[CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19385660Methyl 2-(4-formyl-2-methylphenoxy)phenylacetate

Product 1

HCID 19385606Methyl 2-(4-hydroxymethyl-2-methylphenoxy)phenylacetateYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 1.00 g (3.52 mmol) of the product of Step A dissolved in 14 mL of methanol was treated with 0.067 g (1.8 mmol) of sodium borohydride at room temperature. After 15 minutes the reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid, and the organic layer was separated. The product was washed with water, brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 30% ethyl acetate/hexane to afford 0.660 g (66%) of the title compound.

Workup

  1. customAfter 15 minutes the reaction mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  2. customthe organic layer was separated
  3. washThe product was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-fa32a5d0e0754492a1ae7f21cf8d1c01
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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