Sulfuric Acid → 3-(1,1-difluoroethyl)- Benzenemethanol

HRID 1919805Notes

Reaction equation

HRID 1919805 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[CH3:12])[CH:6]=1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S(=O)(=O)(O)O>C1COCC1>[F:13][C:11]([C:7]1[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[CH:9][CH:8]=1)([F:14])[CH3:12]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 57471636HCID 57471636, compound

Product 1

HCID 574463343-(1,1-difluoroethyl)- BenzenemethanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add a solution of 3-(1,1-Difluoro-ethyl)-benzoic acid ethyl ester (3.57 mmol) in THF (5 mL) dropwise to a 1M solution of lithium aluminum hydride in THF (4.3 mL) at room temperature. Stir for 20 minutes then add ice followed by a mixture of concentrated sulfuric acid and ice (approximately 1:1 v:v). Extract with ethyl ether, dry the organic extracts over sodium sulfate, filter, and evaporate to give the title compound in 97% yield. GCMS MW 172 (M). 1H NMR (400.43 MHz, CDCl3): δ 7.49 (s, 1H), 7.41-7.39 (m, 3H), 4.70 (s, 2H), 1.94-1.85 (m, 3H).

Workup

  1. extractionExtract with ethyl ether
  2. dry with materialdry the organic extracts over sodium sulfate
  3. filtrationfilter
  4. customevaporate

Sources & evidence

ORD record
ord-bd08815dcea1436faca19f85429d6fc2
Source dataset
uspto-grants-2012_05
Patent number
US08168659B2

Reaction notes

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