Toluene → 4-(4-Ethylphenyl)butanoic acid

HRID 53139

Reaction equation

HRID 53139 reaction equation
[CH2:1]([C:3]1[CH:15]=[CH:14][C:6]([C:7]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=O)=[CH:5][CH:4]=1)[CH3:2].C1(C)C=CC=CC=1>O.Cl.[Zn]>[CH2:1]([C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 2

HCID 1140TolueneHCID 3169834-(4-Ethylphenyl)-4-oxobutanoic acid

Product 1

HCID 2316064-(4-Ethylphenyl)butanoic acid

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 313Hydrochloric AcidSolvent3×HCID 962WaterSolvent2×

Procedure

To a 500 mL round-bottomed flask equipped with condenser and nitrogen inlet were added 41.2 grams (200 mmol) 3-(4-ethylbenzoyl)-propionic acid, activated zinc prepared from 82.4 grams (400 mmol) mossy zinc and 8.2 grams mercuric chloride in 125 mL water and 8 mL concentrated hydrochloric acid, 77 mL water, 177 mL concentrated hydrochloric acid, and 100 mL toluene. The mixture was refluxed 60 hours with addition of two 50 mL portions of concentrated hydrochloric acid, cooled, and the layers separated. The organic layer was extracted into 3N aqueous sodium hydroxide, which was then acidified and extracted into ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to afford 28.9 grams (75%), M.P. 70°-72° C.

Workup

  1. customTo a 500 mL round-bottomed flask equipped with condenser and nitrogen inlet
  2. temperaturecooled
  3. customthe layers separated
  4. extractionThe organic layer was extracted into 3N aqueous sodium hydroxide, which
  5. extractionextracted into ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customevaporated
  8. customto afford 28.9 grams (75%), M.P. 70°-72° C.

Sources & evidence

ORD record
ord-a743c1c9f80f4a0eb350e82d1977f3c6
Source dataset
uspto-grants-1997_04
Patent number
US05618811

Linked notes

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