Hydrochloric Acid → HCID 15337437, compound

HRID 2396869Notes

Reaction equation

HRID 2396869 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C1C=CC=CC=1.C(Cl)(=O)C(Cl)=O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([O:20][CH3:21])[CH:17]=[CH:18][C:19]=1[C:5]([C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[OH:2])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 90251,3-DimethoxybenzeneHCID 113702-Methoxybenzoic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15337437HCID 15337437, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 65578Oxalyl chlorideSolvent

Procedure

To a solution 2.0 g (13.14 mmol) of 2-methoxybenzoic acid in 60 ml of dry benzene, 5 ml oxalyl chloride was added under stirring at room temperature. After 2 hours, solvent and excess reagents were removed at reduced pressure. The residual 2-methoxybenzoyl chloride was dissolved in 80 ml of anhydrous ether, and then 1.8 g (13.03 mmol) of 1,3-dimethoxybenzene and 5.0 g of aluminum chloride were added. After stirred at room temperature for 8 hours, the resulting mixture was hydrolyzed by 500 ml of ice water containing 45 ml of concentrated HCl and then extracted with chloroform. The solvent was removed to give a crude product. After purified by column chromatography, 2.20 g (8.53 mmol) of a yellow oily product was obtained and the yield was 65%. The data of the physical properties of the compounds were measured and are listed below.

Workup

  1. customsolvent and excess reagents were removed at reduced pressure
  2. dissolutionThe residual 2-methoxybenzoyl chloride was dissolved in 80 ml of anhydrous ether
  3. stirringAfter stirred at room temperature for 8 hours
  4. extractionextracted with chloroform
  5. customThe solvent was removed
  6. customto give a crude product
  7. customAfter purified by column chromatography

Sources & evidence

ORD record
ord-1f621fc39abb431d92d5502cf6d9301f
Source dataset
uspto-grants-1996_02
Patent number
US05495005

Reaction notes

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