Potassium Hydroxide → HCID 21425481, compound

HRID 1657918Notes

Reaction equation

HRID 1657918 reaction equation
C([O:3][C:4](=[O:37])[C:5]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:27][CH:26]=1)([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:14][CH:13]=1)C(OCC)=O)C.[OH-].[K+]>C(O)C.O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH:5]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:29][CH:30]=2)[C:4]([OH:37])=[O:3])=[CH:13][CH:14]=1)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 635081Propanedioic acid, bis[[4-(2,2-dimethyl-1-oxopropyl)phenyl]methyl]-, diethyl ester

Product 1

HCID 21425481HCID 21425481, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 10g (0.03 mole) of bis-(p-pivaloylbenzyl) malonic acid diethyl ester in 45 ml of ethanol and 45 ml of water, there is added 8.4 g (0.15 mole) potassium hydroxide which is refluxed for 5 hours. The solvents are removed in vacuo and the residue partitioned between ether and water. The aqueous layer is made acidic at 0°C with concentrated hydrochloric acid, extracted with ether, dried and evaporated. The resulting oil is treated with 200 ml of concentrated hydrochloric acid and the mixture is refluxed for 20 hours. The cooled mixture is extracted with ether, the ether extracted with 2N sodium hydroxide and the basic solution is made acidic at 0°C with concentrated hydrochloric acid, extracted with ether, and the ether is then dried and evaporated. The resulting residue is crystallized from ether/petroleum ether to give bis-(p-pivaloylbenzyl) acetic acid, m.p. 107°-109°C.

Workup

  1. temperatureis refluxed for 5 hours
  2. customThe solvents are removed in vacuo
  3. customthe residue partitioned between ether and water
  4. customis made acidic at 0°C with concentrated hydrochloric acid
  5. extractionextracted with ether
  6. customdried
  7. customevaporated
  8. additionThe resulting oil is treated with 200 ml of concentrated hydrochloric acid
  9. temperaturethe mixture is refluxed for 20 hours
  10. extractionThe cooled mixture is extracted with ether
  11. extractionthe ether extracted with 2N sodium hydroxide
  12. customis made acidic at 0°C with concentrated hydrochloric acid
  13. extractionextracted with ether
  14. dry with materialthe ether is then dried
  15. customevaporated
  16. customThe resulting residue is crystallized from ether/petroleum ether

Sources & evidence

ORD record
ord-24300d6dc6ff48e890489d49587a8134
Source dataset
uspto-grants-1976_06
Patent number
US03962320

Reaction notes

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