Pyridine → Methyl 3-acetyl-4-(2'-isopropoxy-5'-methyl-benzoyloxy)-benzoate

HRID 236700Notes

Reaction equation

HRID 236700 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[OH:14])[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].[CH:15]([O:18][C:19]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:20]=1[C:21](Cl)=[O:22])([CH3:17])[CH3:16].N1C=CC=CC=1>O1CCOCC1>[C:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][C:21](=[O:22])[C:20]1[CH:24]=[C:25]([CH3:28])[CH:26]=[CH:27][C:19]=1[O:18][CH:15]([CH3:16])[CH3:17])[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12332833Methyl 3-acetyl-4-hydroxybenzoateHCID 213157482-Isopropoxy-5-methyl-benzoyl chloride

Product 1

HCID 21315729Methyl 3-acetyl-4-(2'-isopropoxy-5'-methyl-benzoyloxy)-benzoateYield 113.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-acetyl-4-hydroxy-benzoate (6 g) in dioxane (100 ml) was reacted with 2-isopropoxy-5-methyl-benzoyl chloride (10 g) in the presence of pyridine (10 ml) at room temperature for 16 hours. After dilution with water, the precipitate was extracted with ethyl acetate and the organic solution was washed with 5% NaHCO3 and water and then evaporated to dryness to give methyl 3-acetyl-4-(2'-isopropoxy-5'-methyl-benzoyloxy)-benzoate (13 g, oil), which was dissolved in methyl-ethyl-ketone (200 ml) and treated with anhydrous potassium carbonate (22 g) under stirring at the reflux temperature for 4 hours.

Workup

  1. extractionAfter dilution with water, the precipitate was extracted with ethyl acetate
  2. washthe organic solution was washed with 5% NaHCO3 and water
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-0b2b14dab56d4bab94d63009b1de3844
Source dataset
uspto-grants-1979_06
Patent number
US04157334

Reaction notes

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