Hydrochloric Acid → HCID 53985323, compound

HRID 2219226Notes

Reaction equation

HRID 2219226 reaction equation
Cl.C([O:4][CH:5](OCC)[CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)C>CCOCC>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([O:7][CH2:6][CH:5]=[O:4])=[CH:9][CH:10]=1)#[N:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 177499644-(2,2-Diethoxyethoxy)benzonitrile

Product 1

HCID 53985323HCID 53985323, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 5N HCl (25 mL) solution is added to a stirred solution of 4-(2,2-diethoxy-ethoxy)-benzonitrile (2.00 g, 8.50 mmol) in Et2O (25 mL). The two-layered solution is stirred vigorously at ambient temperature under nitrogen for 24 hours. Another 50 mL Et2O is added to the mixture. The organic layer is separated, washed with an aqueous solution (30 mL) containing saturated NaHCO3 (0.5 mL), dried over MgSO4, filtered and concentrated at ambient temperature to give 1.36 g of the crude (4-cyano-phenoxy)acetaldehyde as oil. The oil is diluted in Et2O to form a stock solution (25 mg/mL), which is used for the subsequent reaction. 1H NM (CDCl3): δ4.66 (s, 2H), 9.85 (s, 1H).

Workup

  1. customThe organic layer is separated
  2. washwashed with an aqueous solution (30 mL)
  3. additioncontaining saturated NaHCO3 (0.5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated at ambient temperature

Sources & evidence

ORD record
ord-e5a412107ada495a82126dcd886af2b8
Source dataset
uspto-grants-2008_08
Patent number
US07414063B2

Reaction notes

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