Water → 1-(4-Iodophenyl)cyclopropane-1-carboxylic acid

HRID 1722914Notes

Reaction equation

HRID 1722914 reaction equation
S(=O)(=O)(O)[OH:2].[I:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:16]#N)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[OH2:18]>>[I:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:16]([OH:2])=[O:18])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 200261691-(4-Iodophenyl)cyclopropanecarbonitrile

Product 1

HCID 217064771-(4-Iodophenyl)cyclopropane-1-carboxylic acidYield 96%

Procedure

To a mixture of concentrated sulfuric acid (20 ml) and water (30 ml) at room temperature, there was added 1-(4-iodophenyl)cyclopropanecarbonitrile (7.0 g, 0.026 m). The reaction mixture was refluxed for 15 hrs under nitrogen atmosphere. The reaction mixture was cooled to room temperature and extracted with ether-chloroform mixture (4×100 ml). The organic layer was washed with water (2×50 ml), brine (50 ml) and dried over magnesium sulfate. The solvent was removed to give 7.2 g of product (96% yield; M.P. 150°-152° C.). ##STR5## Xn =2-chloro, 6-fluoro.

Workup

  1. temperatureThe reaction mixture was refluxed for 15 hrs under nitrogen atmosphere
  2. extractionextracted with ether-chloroform mixture (4×100 ml)
  3. washThe organic layer was washed with water (2×50 ml), brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-5fd18331e120447fa7c0239e017b9de5
Source dataset
uspto-grants-1989_08
Patent number
US04859232

Reaction notes

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