Potassium Hydroxide → HCID 19363139, compound

HRID 850319Notes

Reaction equation

HRID 850319 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[C:12]([C:20]([O:22]C)=[O:21])[CH:13]=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16].[OH-].[K+]>CO.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[C:12]([CH:11]=1)[C:20]([OH:22])=[O:21]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19363115HCID 19363115, compound

Product 1

HCID 19363139HCID 19363139, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of dimethyl 5-(2-chloro-5-methoxyphenyl)-isophthalate (1.20 g) and potassium hydroxide (0.23 g) in methanol (60 ml) and 1,4-dioxane (20 ml) was refluxed for 48 hours. The mixture was evaporated in vacuo and to the residue was added ethyl acetate and water. Two layers were separated and the aqueous layer was acidified with hydrochloric acid solution. The product was extracted with ethyl acetate and the organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give 5-(2-chloro-5-methoxyphenyl)-3-methoxycarbonylbenzoic acid (0.96 g, 83.5%).

Workup

  1. temperaturewas refluxed for 48 hours
  2. customThe mixture was evaporated in vacuo and to the residue
  3. additionwas added ethyl acetate and water
  4. customTwo layers were separated
  5. extractionThe product was extracted with ethyl acetate
  6. washthe organic layer was washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-cae285a5c2f140ac8f0d73b345132da8
Source dataset
uspto-grants-2000_01
Patent number
US06017917

Reaction notes

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