Acetyl chloride → HCID 12196702, compound

HRID 506961Notes

Reaction equation

HRID 506961 reaction equation
[C:1]([CH2:4][C:5]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(O)=[O:2].C(Cl)(=O)C>CC(C)=O>[CH3:15][O:14][C:11]1[CH:10]=[C:6]2[C:5]([CH2:4][C:1](=[O:2])[O:8][C:7]2=[O:9])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 23054232-(carboxymethyl)-5-methoxybenzoic acid

Product 1

HCID 12196702HCID 12196702, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2-(carboxymethyl)-5-methoxybenzoic acid (5.22 g) (synthesised using the procedure in Tetrahedron 1975, 31, 2607-19) in acetone (50 ml) was added acetyl chloride (7.06 ml) and the reaction mixture was stirred at room temperature for 18 hours. The solvent was evaporated and azeotroped with toluene (×3). The resultant solid was triturated with diethyl ether to yield 7-methoxy-1H-isochromene-1,3(4H)-dione as a brown solid (4.36 g); NMR Spectrum: (DMSOd6) 3.84 (s, 3H), 4.20 (s, 2H), 7.36 (m, 2H), 7.50 (s, 1H).

Workup

  1. customsynthesised
  2. customThe solvent was evaporated
  3. customazeotroped with toluene (×3)
  4. customThe resultant solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-b03248ada40044e7a266c5a37c696810
Source dataset
uspto-grants-2010_08
Patent number
US07786115B2

Reaction notes

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