Cinnamoylbenzene → Dihydrochalcone

HRID 1014769Notes

Reaction equation

HRID 1014769 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)Cl>[C:11]1([C:9](=[O:10])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 7189Cinnamoylbenzene

Product 1

HCID 64802DihydrochalconeYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the general procedure, a solution of chalcone (50 mg, 0.24 mmol) and rac-32 (7.4 mg, 0.0047 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was pressurized with H2 to 62 bar and stirred for 96 h. Filtration of the reaction mixture and evaporation of the solvent gave 41 as a colorless solid (50 mg, 99%). mp 69-70° C. (lit.2 70-72° C.); 1H NMR27 (300 MHz, CDCl3): δ 7.98 (d, 2H, J=7.2 Hz), 7.6-7.2 (m, 8H), 3.33 (t, 2H, J=7.8 Hz), 3.10 (t, 2H, J=7.2 Hz); 13C NMR (75.5 MHz, CDCl3): δ 199.3, 141.4, 136.9, 133.2, 128.7, 128.6, 128.5, 128.1, 126.2, 40.5, 30.2.

Workup

  1. filtrationFiltration of the reaction mixture and evaporation of the solvent

Sources & evidence

ORD record
ord-f9bff3e6afcc4b1882196c3023a2289c
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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