Hydrochloric Acid → Methyl 4-acetylbenzoate

HRID 18201Notes

Reaction equation

[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl.[CH3:14]O>>[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([O:10][CH3:14])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 114704-Acetylbenzoic Acid

Product 1

HCID 137990Methyl 4-acetylbenzoateYield 74%

Conditions

Temperature: -10 °C

Procedure

4-Acetylbenzoic acid (1.00 g, 6.09 mmol) was suspended in methanol (10 mL). Hydrochloric acid (500 μL) was added. The reaction mixture was refluxed overnight. The resulting suspension was cooled to −10° C., filtered and the solid washed with cold methanol (3×2 mL) to provide methyl 4-acetylbenzoate as a white solid (799 mg, 74%). 1H NMR (200 MHz, CDCl3) δ 8.12 (d, J=8.9 Hz, 2H), 8.01 (d, J=8.9 Hz, 2H), 3.95 (s, 3H), 2.65 (s, 3H).

Workup

temperatureThe reaction mixture was refluxed overnight
filtrationfiltered
washthe solid washed with cold methanol (3×2 mL)

Sources & evidence

ORD record: ord-8b017249817a42f396af5c4a28447a78
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741349B2

Reaction notes

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