Water → HCID 86737923, compound

HRID 894180Notes

Reaction equation

HRID 894180 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][O:18][C:12]=3[CH:11]=2)[C:5]([C:19]([O:21]C)=[O:20])=[CH:4][CH:3]=1.[OH-].[Na+].O>CO>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][O:18][C:12]=3[CH:11]=2)[C:5]([C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86737924HCID 86737924, compound

Product 1

HCID 86737923HCID 86737923, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 16.07 gm. (0.044 mole) of methyl 5-bromo-α-(3,4methylenedioxyphenoxy)-o-toluate to a solution of 3.52 gm. (0.088 mole) of sodium hydroxide in 24 ml. of water and 212 ml. of methanol. Heat the mixture under reflux for 1 hour. Remove the methanol under vacuum and dissolve the residue in 225 ml. of water. Acidify with concentrated hydrochloric acid to the congo red end point. Separate the solids by filtration and dry (yield 14.14 gm., m.p. 167°-177° C.). Recrystallize from ethanol-water to obtain pure product as tan needles (m.p. 177°-180° C.).

Workup

  1. additionAdd 16.07 gm
  2. temperatureHeat the mixture
  3. temperatureunder reflux for 1 hour
  4. customRemove the methanol under vacuum
  5. dissolutiondissolve the residue in 225 ml
  6. customSeparate the solids
  7. filtrationby filtration
  8. customdry (yield 14.14 gm., m.p. 167°-177° C.)
  9. customRecrystallize from ethanol-water

Sources & evidence

ORD record
ord-afe6524e381f449da6e42230ee9a0874
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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