Pyridine → Methyl 4-(2-oxiranylmethoxy)benzeneacetate

HRID 1385825Notes

Reaction equation

HRID 1385825 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, 0.030 mol), epichlorohydrin (23.5 ml, 0.30 mol) and pyridine (121 μl, 1.5 mmol) was stirred at 85° C. for 2 hours. 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)
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customThe dark residue was chromatographed (silica, hexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-d8bf09cdb4a6482c870773c585ad8357
Source dataset
uspto-grants-2001_07
Patent number
US06264917B1

Reaction notes

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