Methanol → HCID 19917845, compound

HRID 2184113Notes

Reaction equation

HRID 2184113 reaction equation
C[O:2][C:3]([C:5]1[CH:25]=[C:24]([Br:26])[C:8]2[O:9][C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:11][C:7]=2[C:6]=1[Cl:27])=[O:4].O.[OH-].[Li+].CO>C1COCC1.O>[Br:26][C:24]1[C:8]2[O:9][C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[O:11][C:7]=2[C:6]([Cl:27])=[C:5]([C:3]([OH:4])=[O:2])[CH:25]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 19917984HCID 19917984, compound

Product 1

HCID 19917845HCID 19917845, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

7-Bromo-4-chloro-2,2-diphenyl-benzo[1,3]dioxole-5-carboxylic acid methyl ester (520 mg, 1.16 mmol) is dissolved in THF (6 ml). Lithium hydroxide hydrate (190 mg, 4.64 mmol) in water (6 ml) is added. After addition of methanol (2 ml) the reaction is heated to reflux for 5 hours. After cooling the organic solvents are evaporated and the reaction is diluted with water, acidified with 1N aqueous HCl solution and extracted with ethyl acetate. The combined organic layers are washed with brine, dired over sodium sulfate and filtered. The solvent is evaporated in vacuo. The residue is stirred with n-hexane. The product precipitates as a white solid (350 mg, 70%), which is filtered and dried.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooling the organic solvents
  4. customare evaporated
  5. additionthe reaction is diluted with water
  6. extractionextracted with ethyl acetate
  7. washThe combined organic layers are washed with brine
  8. filtrationfiltered
  9. customThe solvent is evaporated in vacuo
  10. customThe product precipitates as a white solid (350 mg, 70%), which
  11. filtrationis filtered
  12. customdried

Sources & evidence

ORD record
ord-a06de62017f84ec4ba6e2820ed0313fb
Source dataset
uspto-grants-2005_05
Patent number
US06900227B2

Reaction notes

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