2-[2-(3-Methylphenyl)ethyl]benzoic acid → 3-(o-Carboxyphenethyl)ethylbenzene

HRID 596529Notes

Reaction equation

HRID 596529 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[CH:5]=[CH:6][C:7]1[C:8]([C:13]([OH:15])=[O:14])=[CH:9][CH:10]=[CH:11][CH:12]=1.[C:19](C1C=CC=CC=1CCC1C=C(C)C=CC=1)(O)=O>[Pd].CN(C)C=O>[C:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1[CH:1]=[CH:19][CH:16]=[CH:17][CH:18]=1)([OH:15])=[O:14]

Participants

5

Reactant 2

HCID 123988162-[2-(3-Methylphenyl)ethyl]benzoic acidHCID 536852163'-Methylstilbene-2-carboxylic acid

Product 1

HCID 706388133-(o-Carboxyphenethyl)ethylbenzene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 53.0 gm. of 3'-methylstilbene-2-carboxylic acid in 230 ml. dimethylformamide containing 2.0 gm. of 5% palladium on carbon is hydrogenated in a Parr shaker at 60 p.s.i. for 11/2 hours. The solution is filtered and added to ether and water. The organic layer is washed with water, then dried and evaporated. The product is recrystallized from ether-hexane to give 48 gm., 90%, of 3-(o-carboxyphenethyl)toluene, m.p. 82°-84° C. Use of 3'-ethylenestilbene-2-carboxylic acid gives a similar yield of 3-(o-carboxyphenethyl)ethylbenzene.

Workup

  1. custom2 hours
  2. filtrationThe solution is filtered
  3. additionadded to ether and water
  4. washThe organic layer is washed with water
  5. customdried
  6. customevaporated
  7. customThe product is recrystallized from ether-hexane
  8. customto give 48 gm

Sources & evidence

ORD record
ord-d3bb0d69df324b86a1f0febb80e54c83
Source dataset
uspto-grants-1977_03
Patent number
US04011243

Reaction notes

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