Hydrochloric Acid → 2-Acetylbenzoic acid

HRID 1909488Notes

Reaction equation

HRID 1909488 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12](O)(=O)CC(O)=O.Cl>C(N(CC)CC)C>[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])(=[O:5])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 867Malonic Acid2×HCID 6811Phthalic Anhydride

Product 1

HCID 684742-Acetylbenzoic acidYield 281.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of phthalic anhydride (compound of formula (XII)) (2.3 kg, 1 eq) (commercially available), malonic acid (compound of formula (XIII)) (389 g) (commercially available) and triethylamine (3.2 L) were heated to 80° C. Further portions of malonic acid (5×389 g; 1.94 kg total) were charged at 15 minute intervals and the reaction mixture maintained at 80° C. for 10 hrs. 4M hydrochloric acid (12.2 L) was charged and the reaction stirred for a further 30 minutes before being cooled to 25° C. and the resulting slurry filtered. The damp cake was washed with water (2×4 L) before being dried in vacuo at 50° C. to give the title compound (1.73 kg, 68%); 1H NMR (400 MHz, CDCl3): δ 1.97 (3H, s, CH3), 4.13 (1H, br s, OH) 7.52-7.63 (2H, m, CH Ar), 7.69-7.73 (1H, t, CH Ar), 7.84-7.86 (1H, d, CH Ar); 13C NMR (100 MHz, CDCl3) δ 26.0, 106.6, 122.1, 125.4, 126.0, 130.5, 134.8, 149.8 and 169.3.

Workup

  1. temperaturethe reaction mixture maintained at 80° C. for 10 hrs
  2. temperaturebefore being cooled to 25° C.
  3. filtrationthe resulting slurry filtered
  4. washThe damp cake was washed with water (2×4 L)
  5. custombefore being dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-18ca245e64994faf8a715d1f439e85ae
Source dataset
uspto-grants-2013_12
Patent number
US08598387B2

Reaction notes

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