Benzoic Acid → HCID 69822365, compound

HRID 2228346

Reaction equation

HRID 2228346 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH:7]([CH3:13])[CH2:6]2.[NH:14]1C[CH2:17][CH2:16][CH2:15]1.[C:19](O)(=[O:26])C1C=CC=CC=1.[OH2:28].[C:29]1([CH3:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:29]([CH:34]([CH2:33][CH2:32][CH2:31][CH3:30])[CH2:19][O:26][C:17](=[O:28])[C:16]([C:15]#[N:14])=[C:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH2:6][CH:7]1[CH3:13])[CH3:35]

Participants

6

Reactant 5

HCID 243Benzoic AcidHCID 962WaterHCID 1140TolueneHCID 31268PyrrolidineHCID 122904905-Methoxy-2-methylindan-1-one

Product 1

HCID 69822365HCID 69822365, compound

Procedure

The above 2,3-dihydro-5-methoxy-2-methyl-1H-inden-1-one (5.2 g) was reacted with 5.9 g of 2-ethyl-hexyl cyano acetate in the presence of catalytic amounts of pyrrolidine and benzoic acid in 100 ml of toluene. The reaction mixture was refluxed for 30 hours with simultaneous separation of water. Then, the cold reaction mixture was washed with water, concentrated and chromatographed in toluene containing 2% of propanol through SiO2 to yield 2.6 g of a yellow liquid. UV 347 nm (ε=33′450), MS: 355(M+), 243 (100%), 226, 198.

Workup

  1. customThen, the cold reaction mixture
  2. washwas washed with water
  3. concentrationconcentrated
  4. customchromatographed in toluene containing 2% of propanol through SiO2

Sources & evidence

ORD record
ord-2d7fa24983514ab1ab0f9e1ad6ea1384
Source dataset
uspto-grants-2002_07
Patent number
US06416746B1

Linked notes

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