Pyridine → 2-(Acetyloxy)-5-tert-butylbenzoic acid

HRID 454456Notes

Reaction equation

HRID 454456 reaction equation
N1C=CC=CC=1.[C:7](OC(=O)C)(=[O:9])[CH3:8].[C:14]([C:18]1[CH:26]=[C:22]([C:23]([OH:25])=[O:24])[C:21]([OH:27])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl>[C:7]([O:27][C:21]1[CH:20]=[CH:19][C:18]([C:14]([CH3:17])([CH3:15])[CH3:16])=[CH:26][C:22]=1[C:23]([OH:25])=[O:24])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 852815-(1,1-Dimethylethyl)salicylic acid

Product 1

HCID 122744882-(Acetyloxy)-5-tert-butylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.034 mL) and acetic anhydride (0.034 mL) were sequentially added to a methylene chloride (0.54 mL) solution of 5-tert-butylsalicylic acid (0.054 g), followed by stirring at room temperature for 2 hours. The solvent was evaporated under reduced pressure, and 1 mol/L hydrochloric acid and ethyl acetate were added to the residue. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.049 g of 2-acetoxy-5-tert-butylbenzoic acid as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure, and 1 mol/L hydrochloric acid and ethyl acetate
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-393bfbc670f34754be83d7d354a19086
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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