Hydrochloric Acid → HCID 12044475, compound

HRID 1957344Notes

Reaction equation

HRID 1957344 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>[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

6

Reactant 4

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

Product 1

HCID 12044475HCID 12044475, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
150 °C

Procedure

A solution of 3,4-methylenedioxy phenol (7.0 g, 50.7 mmol) in anhydrous DMSO was added dropwise over 30 minutes to a stirred suspension of 60% oil dispersion NaH (2.02 g, 50 mmol) in anhydrous DMSO (40 mL) under nitrogen. Following the addition, a solution of p-fluorobenzaldehyde (6.2 g, 0.05 mol) in DMSO (10 mL) was added, and the temperature was slowly raised to 150° C. The temperature was maintained between 130°-160° C. for 1 hour and then allowed to cool to ambient temperature. After 12 hours at ambient temperature, the reaction mixture was poured onto crushed ice-water and made barely acidic with concentrated HCl and extracted with ether. The combined ether extracts were washed successively with cold dilute aqueous sodium hydroxide solution, cold dilute HCl solution, 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, 300 MHz) δ6.0 (s, 2H), 6.6 (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. additionthe addition
  2. temperatureThe temperature was maintained between 130°-160° C. for 1 hour
  3. temperatureto cool to ambient temperature
  4. additionthe reaction mixture was poured
  5. extractionextracted with ether
  6. washThe combined ether extracts were washed successively with cold dilute aqueous sodium hydroxide solution, cold dilute HCl solution, 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-25d84520e66b4b1aac496bdf7cd2326f
Source dataset
uspto-grants-1998_07
Patent number
US05783593

Reaction notes

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