Hydrochloric Acid → 3,5-Diacetoxybenzoic Acid

HRID 2258480Notes

Reaction equation

HRID 2258480 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([OH:11])[CH:10]=1)[C:5]([OH:7])=[O:6].Cl>C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>[C:2]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][C:5](=[O:6])[CH3:4])[CH:10]=1)[C:5]([OH:7])=[O:6])(=[O:1])[CH3:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 74243,5-Dihydroxybenzoic Acid

Product 1

HCID 5398693,5-Diacetoxybenzoic AcidYield 183.9%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

3,5-Dihydroxybenzoic acid (7.2 g, 50 mM) was dissolved in 11 ml of acetic anhydride. To the resulting solution were added 5 drops of sulfuric acid, followed by stirring at room temperature for 20 minutes. Subsequently, 10 g of ice was added and 12 ml of 1N hydrochloric acid was then added. After sonication, a precipitated crystal was recovered by filtration. Washing the crystal with toluene gave 3,5-diacetoxybenzoic acid (10.23 g). The obtained 3,5-diacetoxybenzoic acid (2.38 g, 10 mM) was dissolved in 5 ml of SOCl2 and the solution was heated under reflux at 80° C. for 1 hour. The solvent SOCl2 was distilled off under reduced pressure to yield 3,5-diacetoxybenzoyl chloride (2.44 g).

Workup

  1. customAfter sonication
  2. filtrationa precipitated crystal was recovered by filtration
  3. washWashing the crystal with toluene

Sources & evidence

ORD record
ord-8d399a0b9a3741749dd356adc9b9bdcd
Source dataset
uspto-grants-1997_08
Patent number
US05661153

Reaction notes

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