Hydrochloric Acid → HCID 12044475, compound

HRID 1781147Notes

Reaction equation

HRID 1781147 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([OH:10])=[CH:4][C:3]=2[O:2]1.[H-].[Na+].F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.Cl>CS(C)=O.O>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([O:10][C:14]3[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=3)=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 68289Sesamol

Product 1

HCID 12044475HCID 12044475, compoundYield 67.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 3,4-methylenedioxyphenol (7.0 g, 50.7 mmol) in anhydrous DMSO (20 mL) was added dropwise over 30 minutes to a stirred suspension of 60% oil dispersion sodium hydride (2.02 g, 50 mmol) in anhydrous DMSO (40 mL) under a nitrogen atmosphere. Upon completion of addition, a solution of p-fluorobenzaldehyde (6.2 g, 50 mmol) in DMSO (10 mL) was added, and the temperature was slowly raised to 150° C. The reaction mixture was maintained at 130°-160° C. for one hour and then allowed to cool to ambient temperature. After 12 hours at ambient temperature, the reaction mixture was poured onto crushed ice and water, made slightly acidic with concentrated hydrochloric acid and extracted with ether. The combined organic extracts were washed with successively with cold dilute aqueous sodium hydroxide, cold dilute hydrochloric acid, ice-cold water and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered, and evaporated to give a red liquid which solidified. The solid was triturated with boiling n-pentane, filtered and washed with boiling pentane to give 8.2 g (67%) of the title compound. m.p. 67°-70° C. 1H NMR (CDCl3, 300MHz) δ 6.0 (s, 2H), S.6 (m, 2H), 6.8 (d, 1H), 7.04 (m, 2H), 7.84 (m, 2H), 9.92 (s, 1H). MS (DCl/NH3) m/e 243 (M+H)+.

Workup

  1. additionUpon completion of addition
  2. temperatureThe reaction mixture was maintained at 130°-160° C. for one hour
  3. temperatureto cool to ambient temperature
  4. additionthe reaction mixture was poured
  5. extractionextracted with ether
  6. washThe combined organic extracts were washed with successively with cold dilute aqueous sodium hydroxide, cold dilute hydrochloric acid, ice-cold water and saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto give a red liquid which
  11. customThe solid was triturated with boiling n-pentane
  12. filtrationfiltered
  13. washwashed with boiling pentane

Sources & evidence

ORD record
ord-9b5e667c8e17468295849f3310e72ee5
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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