Acetic Anhydride → 6-Chloro-8-iodocoumarin

HRID 2120063Notes

Reaction equation

HRID 2120063 reaction equation
[I:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:4]([CH:5]=O)[C:3]=1[OH:11].[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(N(CC)CC)C>[Cl:10][C:8]1[CH:7]=[C:4]2[C:3](=[C:2]([I:1])[CH:9]=1)[O:11][C:12](=[O:14])[CH:13]=[CH:5]2

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 37725455-Chloro-2-hydroxy-3-iodobenzaldehyde

Product 1

HCID 226086266-Chloro-8-iodocoumarinYield 9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 3-iodo-5-chlorosalicylaldehyde (100 g, 0.354 mole), acetic anhydride (300 mL) and triethylamine (54 mL) was heated at reflux for 18 hours. Upon cooling, the desired coumarin precipitated as a dark brown crystalline material. The precipitate was filtered, washed with hexane/ethyl acetate (4:1, 200 mL), and air dried. [Yield: 60 g (55% yield)]. Additional quantities of the desired product (10 g, 9% yield) can be obtained from the filtrate, upon storage.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureUpon cooling
  4. customthe desired coumarin precipitated as a dark brown crystalline material
  5. filtrationThe precipitate was filtered
  6. washwashed with hexane/ethyl acetate (4:1, 200 mL), and air
  7. customdried

Sources & evidence

ORD record
ord-f7e94fa9d4534f989c61a15bb576e279
Source dataset
uspto-grants-2004_02
Patent number
US06689754B1

Reaction notes

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