Sodium sulfate decahydrate → 4-Fluoro-2-(hydroxymethyl)phenol

HRID 1456598Notes

Reaction equation

HRID 1456598 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:16]=[C:12]([C:13](O)=[O:14])[C:11]([OH:17])=[CH:10][CH:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[H-]>O1CCCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([OH:17])=[C:12]([CH:16]=1)[CH2:13][OH:14]

Participants

6

Reactant 4

HCID 62649Sodium sulfate decahydrateHCID 676585-Fluorosalicylic acidHCID 166653HydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 106068384-Fluoro-2-(hydroxymethyl)phenolYield 95.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.98 g of lithium aluminum hydride were added to 50 ml of tetrahydrofuran, and a solution of 5.44 g of 5-fluorosalicylic acid in 50 ml of tetrahydrofuran was then added dropwise at room temperature to the resulting solution. The resulting mixture was then heated under reflux for 1 hour. At the end of this time, it was cooled, and sodium sulfate decahydrate was added in order to decompose any excess hydride. Insoluble substances were removed by filtration. The filtrate was concentrated by evaporation under reduced pressure, and purified by silica gel column chromatography, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 4.72 g (yield 95%) of the title compound as a solid substance.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAt the end of this time, it was cooled
  4. customInsoluble substances were removed by filtration
  5. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  6. custompurified by silica gel column chromatography
  7. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-8dccbb66995e4d1282f40264a5ec0011
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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