Acetyl chloride → Ethyl 5-acetyl-4-hydroxy-3-methylbenzofuran-2-carboxylate

HRID 29414Notes

Reaction equation

HRID 29414 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[C:17](Cl)(=[O:19])[CH3:18]>[Ti](Cl)(Cl)(Cl)Cl.ClC1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([C:17](=[O:19])[CH3:18])=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 20205101Ethyl 5-acetyl-4-hydroxy-3-methylbenzofuran-2-carboxylateYield 59%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

To 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester 0.5 g (2.27 mmol) was added 15 mL of chlorobenzene, 0.27 g (3.4 mmol) of acetyl chloride and 0.63 mL (5.7 mmol) of titanium tetrachloride. The mixture was sealed in a pressure tube and the tube was placed in 95° C. oil bath for 5 h with stirring. The reaction mixture was washed with 0.5N HCl and was extracted with ethyl acetate. Removal of the solvents gave the crude product, which was purified by column chromatography to give 0.33 g (59% yield) of 5-acetyl-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as a white solid.

Workup

  1. customThe mixture was sealed in a pressure tube
  2. customwas placed in 95° C.
  3. customfor 5 h
  4. washThe reaction mixture was washed with 0.5N HCl
  5. extractionwas extracted with ethyl acetate
  6. customRemoval of the solvents
  7. customgave the crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-2be44430397b41dab8f07180b2815339
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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