Hydrochloric Acid → 5-Benzylfuran-2-carbaldehyde

HRID 2080078

Reaction equation

HRID 2080078 reaction equation
[CH2:1]([C:8]1[O:12][C:11]([CH:13]2OCC[O:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O1CCCC1>[CH2:1]([C:8]1[O:12][C:11]([CH:13]=[O:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 231308032-(5-Benzyl-furan-2-yl)-[1,3]dioxolane

Product 1

HCID 124185375-Benzylfuran-2-carbaldehydeYield 78.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The resulting 2-(5-benzyl-furan-2-yl)-[1,3]dioxolane (3.8 g, 16.5 mmol) was suspended in a mixture solution of methanol (15 mL), tetrahydrofuran (10 mL) and 2N hydrochloric acid (15 mL), and the solution was stirred at room temperature for 2 hours. Ethyl acetate and an aqueous solution of sodium bicarbonate were added to the reaction solution, which was then partitioned, the organic layer was washed with water twice and dried over anhydrous sodium sulfate. The solvent was evaporated, and the title compound (2.5 g, 13 mmol) was obtained as a brown oil.

Workup

  1. customwas then partitioned
  2. washthe organic layer was washed with water twice
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-8b5a57d2504e4029977fd7f27426edd2
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Linked notes

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