3-(2-Trifluoromethylphenyl)pentanedioic acid → 4-[2-(Trifluoromethyl)phenyl]oxane-2,6-dione

HRID 406376Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]([CH2:14][C:15]([OH:17])=[O:16])[CH2:10][C:11](O)=[O:12]>C(OC(=O)C)(=O)C>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][C:15](=[O:17])[O:16][C:11](=[O:12])[CH2:10]1

Participants

Conditions

Temperature: 110 °C

Procedure

3-(2-Trifluoromethylphenyl)pentanedioic acid (1.2 g) was dissolved in acetic anhydride (12 mL), and the mixture was stirred at 110° C. for two hours. The oil after concentration under reduced pressure was dissolved in ethyl acetate and washed with a saturated sodium bicarbonate solution and brine. After drying over magnesium sulfate, concentration under reduced pressure gave an orange solid. The solid was recrystallized from ethyl acetate (10 mL) and heptane (70 mL) to obtain the title compound (636 mg) as a white powder.

Workup

concentrationThe oil after concentration under reduced pressure
dissolutionwas dissolved in ethyl acetate
washwashed with a saturated sodium bicarbonate solution and brine
dry with materialAfter drying over magnesium sulfate, concentration under reduced pressure
customgave an orange solid
customThe solid was recrystallized from ethyl acetate (10 mL) and heptane (70 mL)

Sources & evidence

ORD record: ord-8ee7f67ec2964ad59d06b3f81aeb9726
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754100B2

Reaction notes

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