Benzoic Acid → Cyano-(2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-ylidene)acetic Acid Ethyl Ester

HRID 2228341Notes

Reaction equation

HRID 2228341 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].[CH3:17][CH2:18][O:19][C:20]([CH2:22][C:23]#[N:24])=[O:21].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:18]([O:19][C:20](=[O:21])[C:22]([C:23]#[N:24])=[C:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[CH:10]=2)[C:6]([CH3:16])([CH3:15])[CH2:7]1)[CH3:17]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 138129z1-Indanone, 5,6-dimethoxy-3,3-dimethyl-

Product 1

HCID 54568492Cyano-(2,3-dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-ylidene)acetic Acid Ethyl EsterYield 71.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

122 g (0.55 mol) of 2,3-Dihydro-5,6-dimethoxy-3,3-dimethyl-1H-inden-1-one (CAS N.[4136-26-9] for preparation see F. Camps, Z. Naturforsch., B : Anorg. Chem., Org. Chem. (1984), 39B (12), 1801-5), 63,3 g (0.56 mol) of ethyl cyano acetate, 12 g (0.14 mol of piperidine, 12 g (0.1 mol) of benzoic acid and 1000 ml toluene were mixed together and heated under reflux for 48 hours. The reaction mixture was cooled to room temperature, washed with diluted HCl, aqueous Na2CO3, and water and then dried (MgSO4). Removal of the solvent and crystallization from EtOH gave 123.8 g of a yellow solid (m.p.: 148-149° C). Yield: 71%; E1%cm: 790 (1 max.: 367 nm) in EtOH. Solubility: 0.35% in CÉTIOL LC

Workup

  1. custom[4136-26-9] for preparation
  2. temperatureheated
  3. temperatureunder reflux for 48 hours
  4. washwashed with diluted HCl, aqueous Na2CO3, and water
  5. dry with materialdried (MgSO4)
  6. customRemoval of the solvent and crystallization from EtOH

Sources & evidence

ORD record
ord-6780460036344928ad4af2cb78f0fba1
Source dataset
uspto-grants-2002_07
Patent number
US06416746B1

Reaction notes

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