Pyridine → Methyl 4-(2-oxiranylmethoxy)benzeneacetate

HRID 1840227Notes

Reaction equation

HRID 1840227 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH2:13]([CH:15]1[O:17][CH2:16]1)Cl.N1C=CC=CC=1>>[O:17]1[CH2:16][CH:15]1[CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7835EpichlorohydrinHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 12941054Methyl 4-(2-oxiranylmethoxy)benzeneacetateYield 34%

Conditions

Temperature
85 °C

Procedure

A mixture of methyl 4-hydroxyphenylacetate (4.98 g, 0.03 mol), epichlorohydrin (23.5 ml, 0.30 mol) and pyridine (121 μl, 1.5 mmol) was stirred at 85° C. for 2 h. The reaction mixture was cooled, and excess epichlorohydrin was distilled off (rotavapor). The residue was taken up in ethyl acetate, washed with brine and dried (Na2SO4) The solution was filtered and concentrated. The dark residue was chromatographed (silica, hexane/ethyl acetate 7:3) to give 2.25 g (34%) of a colourless oil. 1H (300 MHz) and 13C NMR (75 MHz) spectra were in accordance with the structure.

Workup

  1. temperatureThe reaction mixture was cooled
  2. distillationexcess epichlorohydrin was distilled off (rotavapor)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4) The solution
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. customThe dark residue was chromatographed (silica, hexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-053b65b4112442be88ec0513ba1fb7f5
Source dataset
uspto-grants-2004_01
Patent number
US06680047B2

Reaction notes

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