Diethyl Ether → 3,6-Difluoro-1,2-benzenedimethanol

HRID 1810895Notes

Reaction equation

HRID 1810895 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]2[C:9]=1[C:10](=O)[O:11][C:12]2=[O:18].C(OCC)C.CC(=O)OCC>C1COCC1.O>[F:7][C:8]1[C:9]([CH2:10][OH:11])=[C:13]([CH2:12][OH:18])[C:14]([F:17])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 5139183,6-Difluorophthalic anhydrideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 534143233,6-Difluoro-1,2-benzenedimethanolYield 52.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminium hydride (792 mg, 19.8 mmol) was suspended in THF (6 ml) and cooled in an ice bath. A solution of 4,7-difluoro-isobenzofuran-1,3-dione (730 mg, 3.97 mmol) in THF (6 ml) was added during 5 min. After completion of the reaction (5 min), diethyl ether (30 ml) was added. Subsequently, 2 ml of EA were added in order to decompose excess of lithium aluminium hydride, and thereafter water was slowly added until the alumina salts precipitated. The supernatant was decanted and the precipitate washed twice with EA. The combined extracts were dried over sodium sulfate, filtered and evaporated to dryness to yield 360 mg of the title compound.

Workup

  1. temperaturecooled in an ice bath
  2. additionwas added
  3. customprecipitated
  4. customThe supernatant was decanted
  5. washthe precipitate washed twice with EA
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-f9f3f6afd89445b5baf316419854d6e4
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

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