Hydrochloric Acid → HCID 66818587, compound

HRID 1755117Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 3-fluoro-5-trifluoromethyl-benzoic acid (400 mg, 1.92 mmol) in DMF (2 ml) was added dropwise to a suspension of sodium hydride (60% oily, 235 mg, 5.88 mmol) and pent-4-en-1-ol (506 mg, 5.88 mmol) in DMF (12 ml), and the mixture was stirred at 60° C. Further, this mixture was irradiated in a microwave apparatus (150° C., 20 min). The reaction solution was poured into 0.2 N aqueous hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 3-pent-4-enyloxy-5-trifluoromethyl-benzoic acid (290 mg, 55%).

Workup

customFurther, this mixture was irradiated in a microwave apparatus (150° C., 20 min)
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-9e3bf1d3120a4bc09c8ea5e70707e3eb
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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