HCID 18703984, compound → HCID 13244670, compound

HRID 2288069Notes

Reaction equation

HRID 2288069 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:11][C:10]2[C:9](C(O)=O)=[CH:8][CH:7]=[CH:6][C:5]=2[C:4](=[O:15])[CH2:3]1>N1C2C(=CC=CC=2)C=CC=1.CC(=O)OCC.[Cu]>[CH3:1][C:2]1([CH3:16])[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:15])[CH2:3]1

Participants

5

Reactant 1

HCID 18703984HCID 18703984, compound

Product 1

HCID 13244670HCID 13244670, compoundYield 34.4%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 7047QuinolineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.2 g (10 mmol) of 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid were heated to 180° C. for 5 h with 2.2 g of copper powder in 22 g of quinoline. After cooling, the mixture was diluted with EA, and the copper was filtered off and then washed several times with dil. hydrochloric acid. After concentration of the organic phase in a rotary evaporator and purification by chromatography on silica gel using cyclohexane/EA 6:1, 0.6 g of 3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one was obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe copper was filtered off
  3. washwashed several times with dil. hydrochloric acid
  4. customAfter concentration of the organic phase in a rotary evaporator and purification by chromatography on silica gel

Sources & evidence

ORD record
ord-4761e5ed8730430aacea6330a26e22ab
Source dataset
uspto-grants-2000_07
Patent number
US06087399

Reaction notes

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