Propionic Acid → 2-(5,6-Dimethoxy-3,3-dimethyl-1-indanylidene)-4,4-dimethyl-3-oxo-pentanonitrile

HRID 1271791Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=O)[CH2:7][C:6]2([CH3:16])[CH3:15].[C:17]([CH2:23][C:24]#[N:25])(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].C(O)(=O)CC.C([O-])(=O)C.[NH4+]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[C:23]([C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[C:24]#[N:25])[CH2:7][C:6]2([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 120 °C

Procedure

44 g (0.2 mol) of 5,6-dimethoxy-3,3-dimethyl-1-indanone, 25 g (0.2 mol) of pivaloylacetonitrile, 32 g of propionic acid and 17 g of ammonium acetate are mixed in 80 g of xylene and heated at 120° C. for 7 hours. After the system has been cooled to room temperature and the organic phase has been washed, the xylene is distilled off, and the crude product which remains is recrystallized in methanol. Yield: 50% theory; E1/1730 (λmax 373 nm).

Workup

temperatureAfter the system has been cooled to room temperature
washthe organic phase has been washed
distillationthe xylene is distilled off
customthe crude product which remains is recrystallized in methanol

Sources & evidence

ORD record: ord-eb3f1430fc584b66bb8f417be2d4e2de
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208142B2

Reaction notes

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