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Perfluoro-2,5-dimethyl-3,6-dioxanonanoic acid methyl ester → 1H,1H-2,5-Bis(trifluoromethyl)-3,6-dioxa-perfluorononanol

HRID 505975
Notes
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Reaction equation

HRID 505975 reaction equation
[C:1]([C:5]([C:8]([O:11][C:12]([C:18]([O:21][C:22]([C:28](OC)=[O:29])([C:24]([F:27])([F:26])[F:25])[F:23])([F:20])[F:19])([C:14]([F:17])([F:16])[F:15])[F:13])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2].[BH4-].[Na+]>CC(O)C>[C:1]([C:5]([C:8]([O:11][C:12]([C:18]([O:21][C:22]([CH2:28][OH:29])([C:24]([F:25])([F:26])[F:27])[F:23])([F:20])[F:19])([C:14]([F:17])([F:16])[F:15])[F:13])([F:10])[F:9])([F:7])[F:6])([F:4])([F:3])[F:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 141268Perfluoro-2,5-dimethyl-3,6-dioxanonanoic acid methyl esterHCID 4311764Sodium borohydride

Product 1

HCID 27361501H,1H-2,5-Bis(trifluoromethyl)-3,6-dioxa-perfluorononanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

CF3CF2CF2OCF(CF3)CF2OCF(CF3)COF obtained in Example 2-6 is reacted with methanol in an equimolar amount in the presence of sodium fluoride to obtain CF3CF2CF2OCF(CF3)CF2OCF(CF3)COOCH3. The obtained CF3CF2CF2OCF(CF3)CF2OCF(CF3)COOCH3 is reacted with sodium borohydride in 2-propanol to obtain CF3CF2CF2OCF(CF3)CF2OCF(CF3)CH2OH. The obtained CF3CF2CF2OCF(CF3)CF2OCF(CF3)CH2OH is employed as the compound in Example 2-1 to carry out the same reaction. Further, the same reactions as in Examples 2-2 to 2-6 are carried out to obtain FSO2CF2CF2COF and CF3CF2CF2OCF(CF3)CF2OCF(CF3)COF.

Sources & evidence

ORD record
ord-776ac407fb1f41ea800061b789e94a2b
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07781612B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes