Hydrochloric Acid → HCID 97793, compound

HRID 707737Notes

Reaction equation

HRID 707737 reaction equation
[OH-].[Na+].[CH3:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)=[O:5].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.Cl>C1COCC1.ClCCl.CO.O>[OH:12][C:9]1[CH:10]=[CH:11][C:6]([C:4](=[O:5])[CH:3]=[CH:19][C:18]2[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[CH:7][CH:8]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 74694'-HydroxyacetophenoneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 97793HCID 97793, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium hydroxide (100 g, 2.50 mol) in 1.8 L of a 10:8 mixture of water and methanol was added 4-hydroxyacetophenone (136 g, 1.00 mol). After stirring at room temperature for 30 minutes, 4-Methoxybenzaldehyde (136 g, 1.00 mol) was added to this mixture. The reaction mixture was stirred at 50° C. oil bath for 16 hours. A clear yellow solution resulted which was allowed to stir at room temperature for 30 minutes. 1N HCl aq (500 mL) and 600 mL of a 1:1 mixture of dichloromethane and THF were added to result two layers. The organic layer was washed by saturated NaHCO3 aq. (300 mL×2) and water (300 mL×3) and evaporated to yield orange solid. This solid was washed by 300 mL of EtOAc two times. The resulted yellow solid was dried in vacuo. Yield 133 g (52%). 1H NMR (CDCl3): δ3.85 (s, 3H), 6.93 (m, 4H), 7.47 (d, 1H), 7.50 (d, 2H), 7.75 (d, 1H), 7.96 (d, 2H).

Workup

  1. stirringThe reaction mixture was stirred at 50° C. oil bath for 16 hours
  2. customA clear yellow solution resulted which
  3. stirringto stir at room temperature for 30 minutes
  4. additionwere added
  5. customto result two layers
  6. washThe organic layer was washed by saturated NaHCO3 aq. (300 mL×2) and water (300 mL×3)
  7. customevaporated
  8. customto yield orange solid
  9. washThis solid was washed by 300 mL of EtOAc two times
  10. customThe resulted yellow solid was dried in vacuo

Sources & evidence

ORD record
ord-954c53397e1f40aab6bcef0514626857
Source dataset
uspto-grants-2015_11
Patent number
US09175123B2

Reaction notes

Loading…