Allyl Alcohol → HCID 19787470, compound

HRID 1657276Notes

Reaction equation

HRID 1657276 reaction equation
[C:1]1([CH3:18])[CH:6]=[CH:5][C:4]([CH:7]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.[CH2:19](O)[CH:20]=[CH2:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[C:14]1([CH3:17])[CH:13]=[CH:12][C:11]([CH:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:18])=[CH:2][CH:3]=2)[C:8]([O:10][CH2:21][CH:20]=[CH2:19])=[O:9])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 14798Sodium HydroxideHCID 303144-Methyl-alpha-(4-methylphenyl)benzeneacetic acidHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 19787470HCID 19787470, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2,2-bis(p-tolyl)acetic acid (8.52 g), allyl alcohol (6.6 ml) and p-toluenesulfonic acid monohydrate (0.34 g) in toluene (25 ml) was refluxed for 20 hours with continuous removal of water with Dean-Stark apparatus. After being cooled, the mixture was poured into 1N Sodium hydroxide aqueous solution and extracted with ethyl acetate. The extract was washed with 1N sodium hydroxide aqueous solution, 1N hydrochloric acid and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with methylene chloride as an eluent to give allyl 2,2-bis(p-tolyl)acetate (8.09 g).

Workup

  1. temperatureAfter being cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1N sodium hydroxide aqueous solution, 1N hydrochloric acid and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel with methylene chloride as an eluent

Sources & evidence

ORD record
ord-4c326d1512774874b1cd485ec2cc2e06
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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