Potassium Carbonate → HCID 66685581, compound

HRID 922199Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]\[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[C:13]([O-:16])([O-])=O.[K+].[K+].Cl[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1>CN(C=O)C>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:1][C:2]2[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]\[C:10]([O:12][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([O:16][CH3:13])=[CH:3][CH:4]=3)=[O:11])=[CH:6][CH:7]=2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a 250 mL RB flask fitted with magnetic stirrer was charged with 25 mL of DMF. To the stirred solvent were added (2Z)-3-(4-hydroxyphenyl)prop-2-enoic acid (2 g, 12.18 mmol), K2CO3 (6.67 g, 48.73 mmol) and 1-(chloro methyl)-4-methoxybenzene (3.81 g, 24.36 mmol), stirred at 85° C. for 8 h under nitrogen atmosphere. The RM was concentrated by removal of solvent. The crude was dissolved in ethyl acetate (100 mL). The organic layer was washed with water (50 mL) and saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The product was obtained as white color solid (4.5 g, yield: 91.83%). MS (ESI, 120 eV): m/z=403 (M−H)+; 1H NMR (300 MHz, CDCl3): δ 7.55-7.60 (d, 1H), 7.35-7.38 (d, 2H), 7.25-7.28 (dd, 4H), 6.81-6.88 (m, 5H), 5.09 (s, 2H), 4.92 (s, 2H), 3.73 (s, 6H).

Workup

customTo a 250 mL RB flask fitted with magnetic stirrer
concentrationThe RM was concentrated by removal of solvent
dissolutionThe crude was dissolved in ethyl acetate (100 mL)
washThe organic layer was washed with water (50 mL) and saturated brine solution (50 mL)
dry with materialThe organic layer was dried over anhydrous Na2SO4
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-25380a5352844c9a97c57c0f9af72534
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278915B2

Reaction notes

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