Hydrochloric Acid → 2-[4-(4-Formylphenoxy)-phenyl]-3-p-tolylacrylic acid

HRID 2238256Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1.Cl>CN(C)C(=O)C.O>[CH:31]([C:30]1[CH:33]=[CH:34][C:27]([O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[CH:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)=[CH:28][CH:29]=1)=[O:32]

Participants

Conditions

Temperature: 190 °C

Procedure

To a solution of 38 (7.27 g, 28.6 mmol) and potassium carbonate (8.68 g, 62.9 mmol) in 200 mL N,N-dimethylacetamide was added 4-fluorobenzaldehyde (3.9 mL, 36.4 mmol). The reaction mixture was heated to 190° C. for 1.5 h under argon then cooled to room temperature. The addition of 5% HCl in water to pH 1 resulted in the product separating out as oil. Approximately 50 mL ethyl acetate was added to the mixture which is allowed to stir 16 h. The solid was collected and recrystallized out of toluene, rinsed with hexane and dried under vacuum to yield a white powder (8.1 g, 79.0%). 1H NMR (400 MHz, DMSO-d6) δ 12.71 (s, 1H), 9.94 (s, 1H), 7.97 (d, J=8.8 Hz, 2H), 7.76 (s, 1H), 7.25 (d, J=8.4 Hz, 2H), 7.18 (d, J=6.8 Hz, 2H), 7.16 (d, J=6.4 Hz, 2H), 7.07 (d, J=8.0 Hz, 2H), 6.98 (d, J=8.4 Hz, 2H), 2.25 (s, 3H).

Workup

temperaturethen cooled to room temperature
customresulted in the product
customseparating out as oil
additionApproximately 50 mL ethyl acetate was added to the mixture which
customThe solid was collected
customrecrystallized out of toluene
washrinsed with hexane
customdried under vacuum

Sources & evidence

ORD record: ord-3283e692f7c147eba44d55c3e39789d4
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718682B2

Reaction notes

Loading…