Acetic Anhydride → HCID 4547045, compound

HRID 2233341Notes

Reaction equation

HRID 2233341 reaction equation
[CH2:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([CH:7]=O)[C:5]=1[OH:12])[CH:2]=[CH2:3].CCN(CC)CC.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(OCC)(=O)C>[CH2:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:6]2[C:5]=1[O:12][C:20](=[O:22])[CH:21]=[CH:7]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 141062Benzaldehyde, 2-hydroxy-3-(2-propenyl)-

Product 1

HCID 4547045HCID 4547045, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 3-allylsalicylaldehyde (1.62 g, 10.0 mmol) in acetic anhydride (2 mL) in a 5 mL Emrys process vial was added Et3N (2.0 ml). The reaction was heated at 160° C. for 45 min in an Emrys Optimizer Microwave reactor then was cooled to RT. The reaction was diluted with 50 mL of ethyl acetate, the organic layer was washed with aqueous ammonium chloride, aqueous sodium chloride, dried (Na2SO4), and concentrated. Purification of the residue by flash chromatography on silica gel (gradient elution: 5% to 30% Ethyl acetate/Hexanes) yielded the title compound (750 mg, 40%) as a colorless oil: MS (ES) m/e 186.9 (M+H)+.

Workup

  1. temperaturethen was cooled to RT
  2. washthe organic layer was washed with aqueous ammonium chloride, aqueous sodium chloride
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification of the residue by flash chromatography on silica gel (gradient elution: 5% to 30% Ethyl acetate/Hexanes)

Sources & evidence

ORD record
ord-20b931ed34534304aa1e71ffba2dd053
Source dataset
uspto-grants-2010_05
Patent number
US07709496B2

Reaction notes

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