Acetic Acid → HCID 13013041, compound

HRID 1403373Notes

Reaction equation

HRID 1403373 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([O:11][CH2:12]C(=O)C(=O)C)[CH:3]=1.[CH3:18][C:19]([O-:21])=O.[Na+].[CH3:23]C(O)=O>CC(OC(C)=O)=O.O>[C:19]([O:8][C:6]1[C:5]2[CH:9]=[CH:10][C:2]([CH3:23])=[CH:3][C:4]=2[O:11][CH:12]=1)(=[O:21])[CH3:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 70665220HCID 70665220, compound

Product 1

HCID 13013041HCID 13013041, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4-chloro-2-(2,3-dioxobutoxy)benzoic acid (5 g, 19.48 mmol) in HOAc (80 mL) and Ac2O (100 mL) was added NaOAc (4.2 g, 51.22 mmol). After stirring for 3 h at 150° C., the resulting mixture was dissolved in water (1000 mL), extracted with ethyl acetate (3×200 mL), dried over anhydrous magnesium sulfate and concentrated in vacuo to give 6-methyl-1-benzofuran-3-yl acetate as off-white oil (3.8 g, 85%).

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98536ad5ec0f437fb76c37e11d577311
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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