Dimethylformamide → 3-(o-Carboxyphenethyl)ethylbenzene

HRID 972975Notes

Reaction equation

HRID 972975 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.[CH3:19]N(C)C=O>[Pd]>[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

4

Reactant 2

HCID 6228DimethylformamideHCID 536852163'-Methylstilbene-2-carboxylic acid

Product 1

HCID 706388133-(o-Carboxyphenethyl)ethylbenzene

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

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-7cf88f18b19b43a697228e800167cd1c
Source dataset
uspto-grants-1977_10
Patent number
US04054579

Reaction notes

Loading…