Hydrochloric Acid → 3,6,9,12,15,18,21-Heptaoxatricosanoic acid, 23,23,23-trifluoro-

HRID 1351030Notes

Reaction equation

[F:1][C:2]([F:30])([F:29])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][C:24]([O:26]CC)=[O:25].Cl>[OH-].[Na+].[Cl-].[Na+].O>[F:1][C:2]([F:29])([F:30])[CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][C:24]([OH:26])=[O:25]

Participants

Conditions

Temperature: 20 °C

Procedure

The product of step (e) (400 mg) was dissolved in an aqueous sodium hydroxide solution (0.1M, 10 mL) and the reaction was stirred at 20° C. for 16 hours. The reaction mixture was acidified to pH 2 by the addition of hydrochloric acid (2M), then this was diluted with brine (200 mL) and extracted with dichloromethane (2×200 mL). The combined organic layers were dried and the solvent was removed in vacuo to give the title compound as a colourless oil (330 mg). LC retention time 2.41 mins. Mass spectrum m/z 440 [MNH4+]

Workup

extractionextracted with dichloromethane (2×200 mL)
customThe combined organic layers were dried
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-f7f7d8ede45e4e4290b464edf88f116d
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217409B2

Reaction notes

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