Acetic Acid → HCID 89690143, compound

HRID 714027Notes

Reaction equation

CO[C:3]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:4]=1[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH2:18]([Mg]Cl)[CH2:19][CH3:20].CCOCC.C(O)(=O)C>C1COCC1.O>[CH3:17][O:16][C:15]1[C:3]([CH2:18][CH2:19][CH3:20])=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6]

Participants

Conditions

Temperature: -12 °C

Procedure

To a chilled solution (−34° C.) of tert-butyl 2,3-dimethoxybenzoate (171 g, 718 mmol) in THF (855 mL) add 2 M propylmagnesium chloride in ether (448.5 mL, 897 mmol) dropwise at a rate sufficient to keep the internal temperature below −10° C. Stir the mixture 3.5 h maintaining the temperature near −12° C. Add acetic acid (51.4 mL) dropwise to the mixture while maintaining the temperature below −10° C. and then dilute with water (340 mL). Separate the phases and extract the aqueous phase with methyl-tert-butylether (3×100 mL). Wash the combined organic extracts with brine and concentrate the organic phase in vacuo to yield the title compound (190 g, quantitative) as a colorless oil containing traces of THF and methyl-tert-butylether. 1H NMR (300 MHz, CDCl3) δ 7.24-7.14 (m, 2H), 6.93 (dd, J=1.4, 8.0 Hz, 1H), 3.82 (s, 3H), 2.84-2.79 (m, 2H), 1.59 (m, 11H), 0.97 (t, J=7.4 Hz, 3H).

Workup

customthe internal temperature below −10° C
customSeparate the phases
extractionextract the aqueous phase with methyl-tert-butylether (3×100 mL)
washWash the combined organic extracts with brine
concentrationconcentrate the organic phase in vacuo

Sources & evidence

ORD record: ord-8e29450514b94b32856cd71e02d7272c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187411B2

Reaction notes

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