Potassium Hydroxide → 3-(4-Phenylphenyl)prop-2-enoic acid

HRID 29691

Reaction equation

HRID 29691 reaction equation
C[O:2][C:3](=[O:18])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[K+]>C1COCC1.CO>[C:9]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:10]=[CH:11][C:6]([CH:5]=[CH:4][C:3]([OH:18])=[O:2])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 692086043-Biphenyl-4-yl-acrylic acid methyl ester

Product 1

HCID 254923-(4-Phenylphenyl)prop-2-enoic acidYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-biphenyl-4-yl-acrylic acid methyl ester (9.384 g, 39.38 mmol) in THF (120 ml) and MeOH (80 ml) was added 1N KOH (79 ml) and the mixture refluxed. After 3 h, heating was stopped. The reaction mixture was concentrated to about 50 ml, diluted with water (200 ml) and acidified with 2N HCl (80 ml). EtOAc (1000 ml) was added and the whole mixture heated to boiling to dissolve all solids. After cooling, the layers were separated and the organic layer washed with 1N HCl (2×70 ml), water (3×70 ml), brine (2×50 ml), dried over Na2SO4, filtered, concentrated and dried to give 3-biphenyl-4-yl-acrylic acid (7.393 g, 32.966 mmol, 84%) as a white solid, dec. 223-226° C. 1H NMR (DMSO-d6) δ 6.58 (d, 1H), 7.37-7.53 (m, 3H), 7.62 (d, 1H), 7.70-7.84 (m, 6H), 12.40 (s, 1H); mass spectrum [ES(−)], m/z 223 (M−H)−.

Workup

  1. temperaturethe mixture refluxed
  2. temperatureheating
  3. concentrationThe reaction mixture was concentrated to about 50 ml
  4. additiondiluted with water (200 ml)
  5. additionEtOAc (1000 ml) was added
  6. temperaturethe whole mixture heated
  7. dissolutionto dissolve all solids
  8. temperatureAfter cooling
  9. customthe layers were separated
  10. washthe organic layer washed with 1N HCl (2×70 ml), water (3×70 ml), brine (2×50 ml)
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customdried

Sources & evidence

ORD record
ord-8a6ec0d1cadf4067844245e9ccae4d46
Source dataset
uspto-grants-2008_09
Patent number
US07420083B2

Linked notes

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