Hydrochloric Acid → 5-tert-Butyl-indan-1,2-dione 2-oxime

HRID 656449Notes

Reaction equation

HRID 656449 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[CH2:9][CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[N:15](OCCC(C)C)=[O:16].Cl>CO>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[C:9](=[N:15][OH:16])[CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 110305765-Tert-butyl-2,3-dihydroinden-1-one

Product 1

HCID 865966735-tert-Butyl-indan-1,2-dione 2-oximeYield 137.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-tert-butyl-indan-1-one (9.39 g, 39 mmol) was dissolved in 150 ml methanol. Isoamyl nitrite (5 g, 43 mmol) and conc. HCl (5 ml) were added, and the reaction stirred at ambient temperature for 44 hours. The solvents were removed under vacuum to give 11.67 grams of crude product which was used without further purification. 1H NMR (300 MHz, CDCl3) 7.82 (d, 1H), 7.51 (s, 1H), 7.49 (d, 1H), 3.83 (s, 2H), 3.50 (s, 1H, OH) 1.34 (s, 9H). MS (CSI) m/e 218 (M+H)+, 235 (M+NH4)+

Workup

  1. customThe solvents were removed under vacuum

Sources & evidence

ORD record
ord-05cb67d721d343a18d2b6847161d0119
Source dataset
uspto-grants-2011_12
Patent number
US08071762B2

Reaction notes

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