Lithium hydroxide, monohydrate → 4-Iodocinnamic acid

HRID 1869823Notes

Reaction equation

HRID 1869823 reaction equation
C([O:3][C:4](=[O:14])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][CH:8]=1)C.O.[OH-].[Li+]>CO.O1CCCC1.O>[I:13][C:10]1[CH:9]=[CH:8][C:7]([CH:6]=[CH:5][C:4]([OH:14])=[O:3])=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 541932622-Propenoic acid, 3-(4-iodophenyl)-, ethyl ester

Product 1

HCID 35997884-Iodocinnamic acidYield 100.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl-4-iodo-cinnamate (3.2 g, 10.5 mmol) in methanol (25 mL), tetrahydrofuran (25 mL) and water (15 mL) was treated with lithium hydroxide monohydrate (4.2 g, 100 mmol) and the resulting reaction mixture was stirred at ambient temperature over 2 days. The volatiles were evaporated in vacuo and the residue was neutralized with saturated aqueous ammonium chloride solution. The precipitated solid was filtered, washed with water and hexane and dried to afford the title product as a white solid (2.9 g, 91%). It was used as such for the next step.

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water and hexane
  5. customdried

Sources & evidence

ORD record
ord-f29ffa59d5a748d191146d29d8fe69aa
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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