Water → 2,3,6-Trifluoro-1-ethylbenzene

HRID 2351914Notes

Reaction equation

HRID 2351914 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(C)C=CC(S(O[CH2:17][CH2:18][C:19]2[C:24]([F:25])=[CH:23][CH:22]=[C:21]([F:26])[C:20]=2[F:27])(=O)=O)=CC=1.O.[OH-].[Na+]>C(OCC)C>[F:27][C:20]1[C:21]([F:26])=[CH:22][CH:23]=[C:24]([F:25])[C:19]=1[CH2:18][CH3:17]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 156318391-[2-(p-Toluenesulfonyloxy)ethyl]-2,3,6-trifluorobenzeneHCID 21226445Aluminium lithium hydride

Product 1

HCID 148346762,3,6-Trifluoro-1-ethylbenzeneYield 116.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (5.6 g) is suspended in dry diethyl ether (70 ml) and thereto is added dropwise with stirring a solution of 1-[2-(p-toluenesulfonyloxy)ethyl]-2,3,6-trifluorobenzene (23.3 g) in dry diethyl ether (170 ml) at below 10° C., and the mixture is stirred at room temperature for one hour. To the reaction mixture are added water (5.6 ml), 10% aqueous sodium hydroxide (10.0 ml) and water (5.6 ml) in this order, and the mixture is stirred at room temperature for 30 minutes. The resulting white precipitates are filtered off, and the filtrate is concentrated under atmospheric pressure to give 2,3,6-trifluoro-1-ethylbenzene (13.2 g), as colorless oil.

Workup

  1. additionis added dropwise
  2. stirringthe mixture is stirred at room temperature for 30 minutes
  3. customThe resulting white precipitates
  4. filtrationare filtered off
  5. concentrationthe filtrate is concentrated under atmospheric pressure

Sources & evidence

ORD record
ord-3f0c96ace404432e86f07a365c84f10e
Source dataset
uspto-grants-1989_10
Patent number
US04874764

Reaction notes

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