Peracetic Acid → Methyl 2-(4-acetoxyphenoxy)propanoate

HRID 1085333Notes

Reaction equation

C([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:5]=1)(=O)C.[C:17]([O:20]O)(=[O:19])[CH3:18]>C(O)(=O)C>[C:17]([O:20][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12][CH3:13])=[O:11])=[CH:15][CH:16]=1)(=[O:19])[CH3:18]

Participants

Conditions

Temperature: 58 °C

Procedure

Methyl 2-(4-acetylphenoxy)propanoate (22.4 g, 100.0 mL) is dissolved in acetic acid (100 mL). Purified peracetic acid (19%, 58.0 g, 145.0 mmol) is dropwise added to the reaction at 58° C. and 60 mmHgA. The reaction is refluxed for 10 hours at 58° C. and 60 mm HgA whereupon the reaction is analyzed by GLC. The reaction is cooled to room temperature and concentrated under reduced pressure to give pure methyl 2-(4-acetoxyphenoxy)propanoate (20.13 g) (yield 84%):b.p 96-98° C. at 0.15 mm HgA, IR(neat) 1757.8 (vs); 1H NMR (CDC13) delta 1.58 (d, J=6.9 Hz, 3H), 2.23 (s, 3H), 3.72 (s, 3H), 4.70 (q, J=6.9 Hz, 3H), 6.84 and 6.96 (dd, J=9.2 Hz, 4H).

Workup

temperatureThe reaction is cooled to room temperature
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6424c8ef2e034daa893f73b99fc2e566
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05008439

Reaction notes

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