Potassium Hydroxide → 2'-Chloro-4-biphenylylglycolic acid

HRID 267382Notes

Reaction equation

HRID 267382 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:20])[C:15]([O:17]CC)=[O:16])=[CH:10][CH:9]=1.[OH-].[K+]>C(O)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:20])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21556089Ethyl 2'-chloro-4-biphenylylglycolate

Product 1

HCID 215230142'-Chloro-4-biphenylylglycolic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 0.144 moles of ethyl 2'-chloro-4-biphenylylglycolate dissolved in 220 ml. of isopropanol is added 38 g. (0.7 mole) of potassium hydroxide. This mixture is then heated at reflux temperature in a nitrogen atmosphere. The solution is concentrated in vacuo to a viscous oil, which is then dissolved in 500 ml. of water and filtered. The filtrate is acidified with 10% HCl and the precipitate is taken up in ether. The ether layer is dried, filtered and the filtrate concentrated to dryness. Recrystallization of residue from benzene-cyclohexane 1:1 gives 2'-chloro-4-biphenylylglycolic acid.

Workup

  1. temperatureThis mixture is then heated
  2. temperatureat reflux temperature in a nitrogen atmosphere
  3. concentrationThe solution is concentrated in vacuo to a viscous oil, which
  4. dissolutionis then dissolved in 500 ml
  5. filtrationof water and filtered
  6. dry with materialThe ether layer is dried
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated to dryness
  9. customRecrystallization of residue from benzene-cyclohexane 1:1

Sources & evidence

ORD record
ord-10f30f8f91ca40458e6a5415b9b15da9
Source dataset
uspto-grants-1976_03
Patent number
US03941821

Reaction notes

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