Sulfuric Acid → 3-[2-Methoxy-5-(thien-2-yl)phenyl]-1-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one

HRID 396588Notes

Reaction equation

HRID 396588 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:7][C:4]=1[CH:5]=O.[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][C:18]=1[O:26][CH3:27].S(=O)(=O)(O)O.[Cl-].[Na+]>[OH-].[K+].[Cl-].C([N+](C)(C)C)CCCCCCCCCCCCCCC>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:7][C:4]=1[CH:5]=[CH:24][C:23]([C:20]1[CH:21]=[CH:22][C:17]([OH:16])=[C:18]([O:26][CH3:27])[CH:19]=1)=[O:25]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 2214AcetovanilloneHCID 5234Sodium ChlorideHCID 161159092-Methoxy-5-(thiophen-2-yl)benzaldehyde

Product 1

HCID 694941513-[2-Methoxy-5-(thien-2-yl)phenyl]-1-(4-hydroxy-3-methoxyphenyl)-2-propen-1-oneYield 73%

Reagents, catalysts & solvents 2

HCID 8154Hexadecyltrimethylammonium chlorideCatalystHCID 14797Potassium HydroxideSolvent

Procedure

To a suspension of 2-methoxy-5-(thien-2-yl)benzaldehyde (0.5 g, 2.3 mmol), obtained in the same manner as described in Ex-6A, in 5 N KOH solution was added cetyltrimethyl-ammonium chloride (CTACl, 25% in water, 4 mL, 3.0 mmol) followed by the addition of 4′-hydroxy-3′-methoxyacetophenone (0.38 g, 2.3 mmol). The mixture was stirred at room temperature overnight. Then it was acidified to about pH 1 with 6 M sulfuric acid, saturated with sodium chloride, and extracted with dichloromethane. The organic phase was washed with brine, dried and evaporated. Silica gel chromatography (hexane/ethyl acetate, 3:1 then 1:1) gave 0.61 g (73%) of a foam as the desired 3-[2-methoxy-5-(thien-2-yl)phenyl]-1-(4-hydroxy-3-methoxyphenyl)-2-propen-1-one product, m.p. 142-144° C. 1H-NMR (300 MHz, CDCl3): 8.21 (d, 1H), 7.82 (s, 1H), 7.55-7.75 (m, 4H), 6.85-7.15 (m, 4H), 6.14 (s, 1H), 4.00 (s, 3H), 3.95 (s, 3H).

Workup

  1. customobtained in the same manner
  2. extractionextracted with dichloromethane
  3. washThe organic phase was washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-dcb7a23d74f74ba8afa39e58f03d6772
Source dataset
uspto-grants-2003_08
Patent number
US06608101B1

Reaction notes

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