Hydrochloric Acid → HCID 10333880, compound

HRID 1657277Notes

Reaction equation

HRID 1657277 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([CH:7]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:8]([O:10]CC=C)=[O:9])=[CH:3][CH:2]=1.[H-].[Na+].Cl.[C:25]1(C)[CH:30]=CC=C[CH:26]=1>>[C:17]1([CH3:20])[CH:18]=[CH:19][C:14]([C:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:21])=[CH:6][CH:5]=2)([CH2:30][CH:25]=[CH2:26])[C:8]([OH:10])=[O:9])=[CH:15][CH:16]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1140Toluene2×HCID 24758Sodium hydrideHCID 19787470HCID 19787470, compound

Product 1

HCID 10333880HCID 10333880, compound

Procedure

A solution of allyl 2,2-bis(p-tolyl)acetate (8.00 g) in toluene (40 ml) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil) (1.6 g) in toluene (30 ml) at 130° C. under nitrogen atmosphere, and the mixture was refluxed for 6 hours. After being cooled, the mixture was poured into cooled 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo to give 2,2-bis(p-tolyl)-4-pentenoic acid (4.41 g). It was used for the next reaction without further purification.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureAfter being cooled
  3. additionthe mixture was poured
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-9ab5cbad7540427ba131f946bde6569f
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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