Benzaldehyde → (Diethoxymethyl)benzene

HRID 2038337Notes

Reaction equation

HRID 2038337 reaction equation
C(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])OCC.Cl.C(OCC)C>C(O)C>[CH2:17]([O:16][CH:9]([O:13][CH2:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:18]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 31214Ethyl orthoformate

Product 1

HCID 69884(Diethoxymethyl)benzeneYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of benzaldehyde (6.82 mmol), triethyl orthoformate (3.3 g, 22.5 mmol), and conc. HCl (10 μL, 90 μmol) was refluxed in 3.7 mL of ethanol for 24 hrs. Diethyl ether was added and the organic layer was extracted with 3×2 M NaOH. The organic layer was dried over anhydrous Na2SO4. After removal of diethyl ether under reduced pressure, the crude mixture was distilled under vacuum (55-65° C./0.5 mmHg) to give pure benzaldehyde diethylacetal (82-91% yield). All acetals were characterized by 1H-NMR and used without further purification.

Workup

  1. extractionthe organic layer was extracted with 3×2 M NaOH
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customAfter removal of diethyl ether under reduced pressure
  4. distillationthe crude mixture was distilled under vacuum (55-65° C./0.5 mmHg)

Sources & evidence

ORD record
ord-997fedccb69148a6a3de47e90fe66704
Source dataset
uspto-grants-2013_11
Patent number
US08575359B2

Reaction notes

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