Hydrochloric Acid → (E)-3-(3,4-Dimethoxyphenyl)-1-(3-hydroxyphenyl)-1-propenone

HRID 570994Notes

Reaction equation

HRID 570994 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[OH:13][C:14]1[CH:15]=[C:16]([C:20](=[O:22])[CH3:21])[CH:17]=[CH:18][CH:19]=1.[OH-].[K+].Cl>CCO.CCOC(C)=O.CCCCCC.O.CCO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:6]=[CH:21]/[C:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([OH:13])[CH:15]=2)=[O:22])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8419VeratraldehydeHCID 84873-HydroxyacetophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 5708333(E)-3-(3,4-Dimethoxyphenyl)-1-(3-hydroxyphenyl)-1-propenone

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 19096565Water ethanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 3,4-dimethoxybenzaldehyde AP17380 (400 g, 2.41 moles) and 3′-hydroxyacetophenone AP17381 (328 g, 2.41 moles) in EtOH (3200 mL) was treated with a solution of aqueous KOH (536 g, 1200 mL) over a 1 hour period. The resulting solution was allowed to stir for 16 h at room temperature. The reaction mixture was then treated with EtOH (2000 mL) followed by water (1200 mL). A solution of EtOH/water (3400 mL, 1:1) was then added and the reaction mixture acidified to pH 6 using concentrated HCl (720 mL). After addition of acid, water (4000 mL) was added to induce precipitation. The resulting mixture was left stirring overnight and the solids then filtered, washed with water (2×900 mL) and then hexane (2×800 mL). The product was dried under vacuum for 3 hours and then placed in a vacuum oven at 50° C. for 6 days to provide AP14894 (609 g, 89%) as a yellow solid: mp 138-139° C.; TLC (EtOAc/hexane, 1:1) Rf=0.35; 1H NMR (DMSO-d6, 300 MHz) 9.85 (br s, 1H), 7.71 (d, J=6.6 Hz, 2H), 7.61 (d, J=7.7 Hz, 1H), 7.53 (d, J=1.7 Hz, 1H), 7.47 (d, J=1.7 Hz, 1H), 7.39-7.34 (m, 2H), 7.07-7.00 (m, 2H), 3.87 (s, 3H), 3.82 (s, 3H); 13C NMR (DMSO-d6, 75 MHz) 189.4, 158.2, 151.6, 149.4, 144.7, 139.7, 130.1, 127.9, 124.2, 120.4, 120.2, 119.7, 115.0, 112.0, 111.2, 56.1, 56.0; LRMS (ES+) (M+H)+285; Anal. Calcd for C17H16O4: C, 71.82; H, 5.67. Found: C, 71.55; H, 5.61.

Workup

  1. additionwas added
  2. customprecipitation
  3. waitThe resulting mixture was left
  4. stirringstirring overnight
  5. filtrationthe solids then filtered
  6. washwashed with water (2×900 mL)
  7. customThe product was dried under vacuum for 3 hours
  8. waitplaced in a vacuum oven at 50° C. for 6 days
  9. customto provide AP14894 (609 g, 89%) as a yellow solid

Sources & evidence

ORD record
ord-d84b966f3c9945b3bdbb5a31314ad964
Source dataset
uspto-grants-2015_05
Patent number
US09024028B2

Reaction notes

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