Water → 6-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1986616Notes

Reaction equation

HRID 1986616 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[N:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]21OCC[O:13]2.C(O)(C(F)(F)F)=O.C(Cl)Cl.O>C1(C)C=CC=CC=1>[C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH2:1][C:2](=[O:13])[CH2:3][CH2:4]2)#[N:12]

Participants

5

Reactant 3

HCID 962WaterHCID 21863450Trifluoroacetic acid methylene chlorideHCID 68863993HCID 68863993, compound

Product 1

HCID 162445046-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrileYield 122.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalene]-6′-carbonitrile (230 mg, 1.1 mmol), 20% TFA/CH2Cl2 (4 mL), and H2O (˜0.1 mL) was stirred at room temperature for 16 hours. TLC (50% EtOAc/hexanes) showed no starting material (Rf˜0.95) left and a new spot (Rf˜0.90) formed. The mixture was diluted with toluene (50 mL) and then concentrated in vacuo. The residue was diluted with toluene (50 mL) and concentrated again to give 0.23 g (100%) of 6-cyano-2-tetralone as an orange solid. 1H NMR (300 MHz, CDCl3): δ 7.55 (s, 1H), 7.53 (d, 1H, J=7.8 Hz), 7.24 (d, 1H, J=7.8 Hz), 3.64 (s, 2H), 3.11 (t, 2H, J=6.6 Hz), 2.58 (t, 2H, J=6.6 Hz). As shown by the 1H NMR, the product was >95% pure, thus it was used without further purification.

Workup

  1. waitleft
  2. customa new spot (Rf˜0.90) formed
  3. concentrationconcentrated in vacuo
  4. additionThe residue was diluted with toluene (50 mL)
  5. concentrationconcentrated again

Sources & evidence

ORD record
ord-3bcd42eafed84539af22fdb59965cf01
Source dataset
uspto-grants-2009_06
Patent number
US07550467B2

Reaction notes

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