Acetic Acid → Methyl 2-acetyl-3,5-diallyloxyphenylacetate

HRID 499869

Reaction equation

[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:8]=[C:9]([O:11][CH2:12][CH:13]=[CH2:14])[CH:10]=1)[CH:2]=[CH2:3].[C:20](O)(=[O:22])[CH3:21].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>FC(F)(F)C(O)=O>[C:20]([C:8]1[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[CH:10][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:6][C:7]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])(=[O:22])[CH3:21]

Participants

Conditions

Temperature: 4 °C

Procedure

Methyl 3,5-diallyloxyphenylacetate (40 g, 0.14 mol) obtained in Example 5, Step 1 was dissolved in trifluoroacetic acid (0.15 L). After the solution was cooled to 4° C., acetic acid (9.5 mL, 0.17 mol) and trifluoroacetic anhydride (40 mL, 0.28 mol) were added thereto, followed by stirring at 4° C. for 3.5 hours. The reaction mixture was gradually added to a saturated aqueous solution of sodium hydrogencarbonate for neutralization, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/20-1/6) to obtain methyl 2-acetyl-3,5-diallyloxyphenylacetate (30 g, 65%).

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/20-1/6)

Sources & evidence

ORD record: ord-7e45bf1e3f5e448c849e1aa7fa713d8f
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767693B2

Linked notes

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