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

HRID 2399485Notes

Reaction equation

HRID 2399485 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-93316fe2c4d44b1e9d6892c4331f1366
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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