Acetic Anhydride → HCID 66991265, compound

HRID 454460Notes

Reaction equation

HRID 454460 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[OH:8][C:9]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH3:21])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]>C(Cl)Cl.N1C=CC=CC=1>[C:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH3:21])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic Anhydride2×HCID 5080667HCID 5080667, compound

Product 1

HCID 66991265HCID 66991265, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.069 mL) was added to a solution mixture of the obtained 2-hydroxy-5-propoxybenzoic acid (0.12 g) in methylene chloride (3.0 mL) and pyridine (0.12 mL) under ice-cooling, followed by stirring at room temperature for 2 hours and 30 minutes. Pyridine (0.050 mL) and acetic anhydride (0.058 mL) were added to the reaction mixture, followed by stirring at room temperature for 50 minutes. The solvent was evaporated under reduced pressure, and 1 mol/L hydrochloric acid and ethyl acetate were added to the obtained 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: 65-55% hexane/ethyl acetate] to obtain 0.091 g of 2-acetoxy-5-propoxybenzoic acid as a white solid.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 50 minutes
  3. customThe solvent was evaporated under reduced pressure, and 1 mol/L hydrochloric acid and ethyl acetate
  4. additionwere added to the obtained residue
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [eluent: 65-55% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-c863e4bdef364cff8f4224da9e3b0d18
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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