# US 2010/0168480 A1 · Method for producing fluoroalkyl alcohol

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- Number: US 2010/0168480 A1
- Document ID: US20100168480A1
- Status: Published application
- Kind: A1
- Application number: 12/451,659
- Filed: 2008-05-23
- Published: 2010-07-01
- Earliest claimed: 2007-05-28
- Assignees: Daikin Industries, Ltd.
- Inventors: Akinari Sugiyama; Atsushi Suzuki; Masahiro Tomita
- Web page: https://patentgrep.com/patent/US20100168480A1

## CPC

- C07C 29/00: Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention provides a method for producing a fluoroalkyl alcohol represented by general formula (6) wherein Rf1 and Rf2 are the same or different, each represents a CF3(CF2)n group (wherein n is an integer of 0 to 10) or a CH3(CH2)m group (wherein m is an integer of 0 to 10), and at least one of Rf1 and Rf2 represents a CF3(CF2)n group, the method comprising: decarboxylating a compound represented by general formula (1) wherein Rf1 and Rf2 are the same as above; and R1 represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, an alkali metal, or M1/2 (wherein M represents an alkaline earth metal), in the presence of at least one member selected from the group consisting of pyridines, amines, quaternary ammonium salts, and quaternary phosphonium salts. According to the present invention, fluoroalkyl alcohol such as hexafluoroisopropyl alcohol can be easily produced with high selectivity, using an inexpensive starting material.

## Claims

### Claim 1

A method for producing a fluoroalkyl alcohol represented by general formula (6)
wherein Rf1 and Rf2 are the same or different, each represents a CF3(CF2)n group (wherein n is an integer of 0 to 10) or a CH3(CH2)m group (wherein m is an integer of 0 to 10), and at least one of Rf1 and Rf2 represents a CF3(CF2)n group,
the method comprising: decarboxylating a compound represented by general formula (1),
wherein Rf1 and Rf2 are the same as above; and R1 represents an optionally substituted alkyl group, an optionally substituted aryl group, an optionally substituted aralkyl group, an alkali metal, or M1/2 (wherein M represents an alkaline earth metal), in the presence of at least one member selected from the group consisting of pyridines represented by general formula (2)
wherein X represents a halogen atom, and a is an integer of 0 to 9,
amines represented by general formula (3)
wherein R2, R3, and R4 are the same or different, and each represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted aralkyl group; x represents a halogen atom; and b is an integer of 0 to 9,
quaternary ammonium salts represented by general formula (4)
wherein R5, R6, R7, and R8 are the same or different, and each represents an alkyl group, a phenyl group, or a benzyl group; and
X represents a halogen atom, and
quaternary phosphonium salts represented by general formula (5)
wherein R9, R10, R11, and R12 are the same or different, and each represents an alkyl group, a phenyl group, or a benzyl group; and
X represents a halogen atom.

### Claim 2 (depends on 1)

The method for producing a fluoroalkyl alcohol according to claim 1, wherein, in general formula (1), n and m in Rf1 and Rf2 are each 0 or 1; and R1 represents a C1-4 alkyl group, cycloalkyl group, phenyl group, Li, Na, K, or M1/2 (wherein M is Mg, Ca, or Ba).

### Claim 3 (depends on 1)

The method for producing a fluoroalkyl alcohol according to claim 1, wherein, in general formula (3), R2, R3, and R4 are the same or different, and each represents a C1-4 alkyl group.

### Claim 4 (depends on 1)

The method for producing a fluoroalkyl alcohol according to claim 1, wherein,
in general formula (2), X is F, Cl, Br, or I; when R1 in general formula (1) represents an alkali metal or M1/2, a is 0, and when R1 represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted aralkyl group, a is 1 in the case where X represents Cl, Br or I, or a is an integer of 1 to 9 in the case where X represents F; and
in general formula (3), X is F, Cl, Br, or I; when R1 in general formula (1) is an alkali metal or M1/2, b is 0, and when R1 represents an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted aralkyl group, b is 1 in the case where X represents Cl, Br or I, or b is an integer of 1 to 9 in the case where X represents F.

### Claim 5 (depends on 1)

The method for producing a fluoroalkyl alcohol according to claim 1, wherein the decarboxylation reaction is performed in the presence of an amide solvent.