Acetic Anhydride → HCID 59570155, compound

HRID 2071098Notes

Reaction equation

HRID 2071098 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:9]=1)[CH:5]=[O:6].[CH3:13][C:14](OC(C)=O)=[O:15]>N1C=CC=CC=1>[C:14]([O:1][C:2]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:4]([CH:5]=[O:6])[CH:3]=1)(=[O:15])[CH3:13]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 574477143-Hydroxy-5-(propan-2-yl)benzaldehyde

Product 1

HCID 59570155HCID 59570155, compoundYield 113.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 33.2 mg (0.202 mmol) of 3-hydroxy-5-isopropylbenzaldehyde and 50 μL (0.53 mmol) of Ac2O in 3 mL of pyridine was stirred at r.t. for 70 min. The solution was concentrated, water and EtOAc were added, and the layers were separated. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated, and purified by flash silica gel chromatography (20% EtOAc/hexanes) (neutral silica gel) to provide 47.4 mg of 3-formyl-5-isopropylphenyl acetate as a yellow oil with some impurity.

Workup

  1. concentrationThe solution was concentrated
  2. additionwater and EtOAc were added
  3. customthe layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash silica gel chromatography (20% EtOAc/hexanes) (neutral silica gel)

Sources & evidence

ORD record
ord-a945496c276f4534b48ffed1bc2ea1bc
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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