Hydrochloric Acid → HCID 69720667, compound

HRID 279136Notes

Reaction equation

HRID 279136 reaction equation
[C:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:13])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].Cl>O.CN(C)C=O>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][CH2:21][C:4]1([C:1](=[O:3])[CH3:2])[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:13])[CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 68320Ethyl 3-bromopropionateHCID 2191462-acetyl-2,3-dihydro-1h-inden-1-one

Product 1

HCID 69720667HCID 69720667, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
52.5 °C

Procedure

2-Acetyl-1-indanone (15 g, cf. Liebigs Ann. Chem. 347 (1906) 112) was added into a mixture of potassium carbonate (8.5 g) and dry N,N-dimethylformamide (45 ml). The mixture was stirred at 50-55° C. for 20 minutes and ethyl 3-bromopropionate (19 g) was then added and the stirring was continued at 50-55° C. for 6 hours. Water (60 ml) was added to the reaction mixture and the pH of the solution was adjusted to 2-3 with hydrochloric acid. The mixture was stirred at 50-55° C. for one hour. The cooled solution was extracted with toluene, washed with water, dried with sodium sulfate, and the solvent removed under reduced pressure. The yield was 23.5 g.

Workup

  1. waitthe stirring was continued at 50-55° C. for 6 hours
  2. stirringThe mixture was stirred at 50-55° C. for one hour
  3. extractionThe cooled solution was extracted with toluene
  4. washwashed with water
  5. dry with materialdried with sodium sulfate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1a4392eb407c4312a4708ae09199e117
Source dataset
uspto-grants-2002_03
Patent number
US06362211B1

Reaction notes

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