4-Hydroxybenzoic Acid → Benzoic acid, 4-(acetyloxy)-

HRID 2375231Notes

Reaction equation

HRID 2375231 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:17](Cl)(=[O:19])[CH3:18]>Cl>[C:17]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 1049PyridineHCID 6367Acetyl chloride

Product 1

HCID 16865Benzoic acid, 4-(acetyloxy)-Yield 82.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a mixture of 4-hydroxybenzoic acid (16) (20.0 g, 144.8 mmol) and pyridine (60 ml, 742 mmol) at 0° C. was added acetyl chloride (12 ml, 169 mol) over 5 minutes. The resulting mixture was stirred at ice bath temperature for 30 minutes and for 1 hour at room temperature. The mixture was poured into ice water (500 ml) and the pH of the medium was brought to 1-2 by adding conc. HCl (ca. 40 ml). The precipitate was filtered, washed with water (100 ml), and dried (Na2SO4). The obtained solid material was crystallized from methanol-water (1:1) (200 ml) affording the title compound (21.485 g, 82.3%) as white crystals, m.p. 181-183° C. 1H NMR (CDCl3, HMDSO) δ: 2.32 (3H, s); 7.22 (2H, d, J=8.2 Hz); 8.16 (2H, d, J=8.2 Hz); 10.50 (1H, brs).

Workup

  1. waitfor 1 hour at room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with water (100 ml)
  4. dry with materialdried (Na2SO4)
  5. customThe obtained solid material was crystallized from methanol-water (1:1) (200 ml)

Sources & evidence

ORD record
ord-4696cd7da55c438b9f628ae163c02e58
Source dataset
uspto-grants-2008_12
Patent number
US07465719B2

Reaction notes

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