Water → (2,2-Difluoro-1,3-dioxaindan-5-yl)methanol

HRID 529994Notes

Reaction equation

HRID 529994 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1([F:20])[O:12][C:11]2[CH:13]=[CH:14][C:15]([C:17](O)=[O:18])=[CH:16][C:10]=2[O:9]1.O.[OH-].[Na+]>C1COCC1>[F:20][C:8]1([F:7])[O:12][C:11]2[CH:13]=[CH:14][C:15]([CH2:17][OH:18])=[CH:16][C:10]=2[O:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 6087722,2-Difluoro-1,3-benzodioxole-5-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 12814281(2,2-Difluoro-1,3-dioxaindan-5-yl)methanolYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (12.6 g, 0.33 mol) in THF (100 mL) was added dropwise a solution of 2,2-difluorobenzo-1,3dioxole-5-carboxylic acid (30 g, 0.15 mol) in THF (200 mL) at 0□ under N2. The mixture was allowed to warm to room temperature and stirred for one hour at this temperature. Then, water (12.6 g) and aq. NaOH (10%, 12.6 g) were added dropwise at 0□. The resulting mixture was filtered. The filtrate was dried over anhydrous Na2SO4 and evaporated under vacuum to give crude (2,2-difluoro-1,3-benzodioxol-5-yl)methanol (25.5 g, 91.3%), which was used directly in the next step.

Workup

  1. filtrationThe resulting mixture was filtered
  2. dry with materialThe filtrate was dried over anhydrous Na2SO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-0826ea08e9cf43bca73e2588afc4e390
Source dataset
uspto-grants-2016_05
Patent number
US09351962B2

Reaction notes

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