Piperidine → Chromanone

HRID 862474Notes

Reaction equation

HRID 862474 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].N1CCCC1.N1CCCCC1.N1CC[O:25][CH2:24]C1>C1(C)C(C)=CC=CC=1.C1(C)C=CC=CC=1.ClC1C=CC=CC=1.C1C=CC=CC=1>[O:25]1[C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3](=[O:4])[CH2:2][CH2:24]1

Participants

9

Reactant 4

HCID 8082PiperidineHCID 8083MorpholineHCID 31268PyrrolidineHCID 68490alpha-Hydroxyacetophenone2×

Product 1

HCID 68110Chromanone

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 1140TolueneSolventHCID 7237O-XyleneSolventHCID 7964ChlorobenzeneSolvent

Procedure

2-Hydroxyacetophenon (compound 1, R1 is as defined above) and compound 2 wherein R2 and R3 are as defined above are refluxed under heating in a solvent such as benzene, chlorobenzene, toluene and xylene, in the presence of a secondary amine such as pyrrolidine, piperidine and morpholine, using a Dean-Stark apparatus, while removing liberated water to give 4-chromanon (compound 3 wherein R1, R2 and R3 are as defined above).

Workup

  1. temperatureabove are refluxed
  2. customwhile removing liberated water

Sources & evidence

ORD record
ord-8a00874fe6d646749b84b530369c63ff
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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