Water → HCID 86737921, compound

HRID 894176Notes

Reaction equation

HRID 894176 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=2)[C:5]([C:19]([O-:21])=[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][CH:13]=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=2)[C:5]([C:19]([OH:21])=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86737922HCID 86737922, compound

Product 1

HCID 86737921HCID 86737921, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 23.79 gm. (0.0655 mole) of 5-bromo-α-(3-isopropylphenoxy)-o-toluate to a solution of 5.24 gm. (0.1310 mole) of sodium hydroxide in 35 ml. of water and 315 ml. of methanol. Heat at reflux for 3 hours. Remove the methanol under vacuum and dilute the residual solution with 300 ml. of water. Extract with ether. Separate the aqueous layer and acidify with concentrated hydrochloric acid to the Congo Red end point. Extract the resulting oil into ether, wash with water and dry over magnesium sulfate. Remove the solvent under vacuum and allow the resulting oil (21.33 gm.) to stand overnight. Wash the solids formed with petroleum ether to obtain the title compound [yield 10.94 gm., m.p. 103°-122° C., pmr (CDCl3) 1.20(6H,d,(CH3)2CH--), 2.82(1H,m, (CH3)2CH--), 5.47(2H,s,CH2O--), 9.18 (1H, broad s, COOH)].

Workup

  1. additionAdd 23.79 gm
  2. temperatureHeat
  3. temperatureat reflux for 3 hours
  4. customRemove the methanol under vacuum
  5. additiondilute the residual solution with 300 ml
  6. extractionExtract with ether
  7. customSeparate the aqueous layer
  8. extractionExtract the resulting oil into ether
  9. washwash with water
  10. dry with materialdry over magnesium sulfate
  11. customRemove the solvent under vacuum
  12. washWash the solids
  13. customformed with petroleum ether

Sources & evidence

ORD record
ord-1d8fc7adc99845449880367d0fa07c4b
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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