Hydrochloric Acid → HCID 19610222, compound

HRID 1602172Notes

Reaction equation

HRID 1602172 reaction equation
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH:12]=[CH:13][O:14]C)[CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(OCC)C>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([CH2:12][CH:13]=[O:14])[CH2:8][CH2:9][C:10]#[N:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54024114HCID 54024114, compound

Product 1

HCID 19610222HCID 19610222, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4,4-diphenyl-6-methoxyhex-5-enenitrile (4.0 g, 14.4 mmol) in diethylether (60 mL) was added HCl (2 mL, 37 %). The reaction mixture was stirred at room temperature for 16 hr and then the solvent was evaporated in vacuo . The residue was dissolved in dichloro- methane and filtered through a plug of silica gel to give the desired aldehyde as an oil (3.78 g, 99%): 1H-NMR (CDCl3, δ): 2.03-2.10 (m, 2H), 2.56- 2.64 (m, 2H), 3.12 (d, J=3 Hz, 2H), 7.14-7.41 (m, 1OH), 9.34 (t, J=3 Hz, 1H). Anal. Calcd for C1 8HI7NO: C, 82.10; H, 6.51; N, 5.32. Found: C, 82.10; H. 7.02; N. 4.78.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in dichloro- methane
  3. filtrationfiltered through a plug of silica gel

Sources & evidence

ORD record
ord-314d5b4154e349d0bdaae41e4073248f
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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