2,3,6-Trifluorobenzoic acid → 2,3,6-Trifluorobenzyl alcohol

HRID 1722292Notes

Reaction equation

HRID 1722292 reaction equation
B.[Na].[F:3][C:4]1[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[C:5]=1[C:6](O)=[O:7]>O1CCCC1>[F:14][C:9]1[C:10]([F:13])=[CH:11][CH:12]=[C:4]([F:3])[C:5]=1[CH2:6][OH:7]

Participants

4

Reactant 2

HCID 5200622,3,6-Trifluorobenzoic acidHCID 178418435HCID 178418435, compound

Product 1

HCID 1455002,3,6-Trifluorobenzyl alcoholYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of sodium boron hydride (51.6 g) in tetrahydrofuran (500 ml) is added dropwise a solution of 2,5,6-trifluorobenzoic acid (120 g) in tetrahydrofuran (200 ml) with stirring at below 10° C., and thereto is further added dropwise a solution of BF3 ·(C2H5)2O (232 ml) in tetrahydrofuran (500 ml) under ice cooling. The mixture is stirred at room temperature overnight. The reaction mixture is poured into ice water (1.5 liter) and is extracted with diethyl ether. The extract is dried over magnesium sulfate and the solvent is distilled off under reduced pressure to give 2,3,6-trifluorobenzyl alcohol (112.7 g), as pale yellow oil, b.p. 112° C. (30 mmHg).

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. extractionis extracted with diethyl ether
  3. dry with materialThe extract is dried over magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-a0d0a6f2d3334cd085901328c37f23f4
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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