Ammonia → HCID 131728292, compound
Reaction equation
[OH-].[Na+].Cl.[C:4]([C:8]([C:11]([O:14][CH:15]([C:17]([O:20][CH2:21][C:22]([C:25]([OH:27])=[O:26])([F:24])[F:23])([F:19])[F:18])[F:16])([F:13])[F:12])([F:10])[F:9])([F:7])([F:6])[F:5].[NH3:28]>>[C:4]([C:8]([C:11]([O:14][CH:15]([C:17]([O:20][CH2:21][C:22]([C:25]([O-:27])=[O:26])([F:24])[F:23])([F:19])[F:18])[F:16])([F:13])[F:12])([F:10])[F:9])([F:7])([F:6])[F:5].[NH4+:28]Participants
Procedure
The HOCH2CF2COOEt (30 g) obtained by the method described in Synthesis Example 1, tert-BuOK (1.5 g), tert-BuOH (10 g) and a stirrer bar were placed in a 300-ml four-necked flask equipped with a dropping funnel, cold finger and thermometer. After several repetitions of replacement of the flask inside atmosphere with nitrogen, CF3CF2CF2OCF═CF2 (51.8 g) was added dropwise at 20-25° C. over 5 hours while the flask contents were stirred with the magnetic stirrer. Then, after overnight stirring, the flask contents were washed with several portions of a 10% (by weight) aqueous solution of HCl and several portions of a saturated aqueous solution of sodium chloride, then dried over magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure to give 62.1 g of a mixture of CF3CF2CF2OCHFCF2OCH2CF2COOEt and CF3CF2CF2OCHFCF2OCH2CF2COOH. The structures of these compounds were identified by 1H-NMR, 19F-NMR and 13C-NMR. This mixture was subjected to hydrolysis with a 6 N aqueous solution of sodium hydroxide, the hydrolysis product was lyophilized and then neutralized with 12 N hydrochloric acid, and the thus-obtained CF3CF2CF2OCHFCF2OCH2CF2COOH was neutralized with aqueous ammonia and the neutralization product was lyophilized to give 47.3 g of CF3CF2CF2OCHFCF2OCH2CF2COONH4.
Sources & evidence
- ORD record
- ord-484f7c7181be41a29fda9c00912c2f89
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07777075B2
Reaction notes
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