Water → (E)-methyl 3-(3,5-difluoro-4-formylphenyl)acrylate

HRID 1749014Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:4]([F:14])[C:3]=1[CH:15]([OH:20])S([O-])(=O)=O.[Na+].C(=O)([O-])[O-].[K+].[K+].O>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[C:4]([F:14])[C:3]=1[CH:15]=[O:20]

Participants

Conditions

Temperature: 25 °C

Procedure

Under an atmosphere of nitrogen, sodium {2,6-difluoro-4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]phenyl}(hydroxy)methanesulfonate (1.211 kg, 3.52 mol) was to a 100 L vessel followed by potassium carbonate (0.974 kg, 7.05 mol). Water (9.1 L) was added and the agitator was started. Ethyl acetate (9.1 L) was added. The mixture was agitated at 25° C. for 5 hours. The agitator was stopped and the mixture was allowed to stand for 14 hours at 25° C. The lower aqueous phase was removed and discarded. The upper organic phase was concentrated under reduced pressure to afford a pale brown solid. The solid was dried in vacuo to afford (E)-methyl 3-(3,5-difluoro-4-formylphenyl)acrylate as a brown solid (608 g, 76%). 1H NMR (500 MHz, DMSO, 27° C.) δ 3.77 (3H, s), 6.94 (1H, d), 7.66 (1H, d), 7.71 (2H, d), 10.20 (1H, s).

Workup

waitto stand for 14 hours at 25° C
customThe lower aqueous phase was removed
concentrationThe upper organic phase was concentrated under reduced pressure
customto afford a pale brown solid
customThe solid was dried in vacuo

Sources & evidence

ORD record: ord-b9e96af7714445fa8d003fb6a51d4a4c
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09155727B2

Reaction notes

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