3-Phenylprop-2-Enal → HCID 4199240, compound

HRID 1108292Notes

Reaction equation

HRID 1108292 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](OC)=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[CH:13](=O)[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].Cl.[CH3:26]O>O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:26])=[CH:4][C:3]=1[C:10](=[O:12])[CH:11]=[CH:13][CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 3073-Phenylprop-2-EnalHCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-one

Product 1

HCID 4199240HCID 4199240, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2'-Hydroxy-5'-methoxyacetophenone (4.1 g, 22 mmole) and cinnamaldehyde (3.35 g, 25 mmole) were dissolved in minimum methanol (2.5 mL). Concentrated sodium hydroxide (12.5 mL, 50%) was added, and the mixture was kept on ice for 8 hr. The resultant solid was suspended in water and acidified using HCl (4N). The oil that separated was dissolved in ethanol and crystallized from ethanol/water to give 1-(2-hydroxy-5-methylphenyl)-5-phenylpenta-2,4-dien-1-one (1.2 g) as red-brown powder. Mass (CI--NH3) m/z 281 (M++1, base). 1H NMR (CDCl3).3.9(s, 3H, CH3),6.95-7.8(m, 12H). The above compound (170 mg, 0.6 mmole) was dissolved in a mixture of ethanol (3.5 mL) and acetone (4 mL). Sodium hydroxide 1N (1 mL) and hydrogen peroxide (1 mL, 35%) were added, and the solution was stirred 6 hr. at room temperature. The mixture was precipitated by adding water and HCl and purified on preparative TLC (petroleum ether-ethyl acetate) to give compound 15, mp 160-163° C. mass (CI NH3) m/z 297(M++1,base). 1H NMR (CDCl3) 3.9(s,3H,CH3), 4.45(d,J=12 Hz,1H), 4.8(m,1H), 6.55(dd,1H), 6.9-7.6(m,9H).

Workup

  1. customThe oil that separated
  2. dissolutionwas dissolved in ethanol
  3. customcrystallized from ethanol/water

Sources & evidence

ORD record
ord-1992c81aa3c54c90bbd9d124cdb12c5c
Source dataset
uspto-grants-2000_05
Patent number
US06066642

Reaction notes

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