Hydrochloric Acid → 5-Formyl-2-isobutoxyphenyl acetate

HRID 2249690Notes

Reaction equation

HRID 2249690 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH:12]([CH3:14])[CH3:13])[CH:5]=[O:6].[H-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18].Cl>CN(C)C=O.O.C(OCC)(=O)C>[C:17]([O:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH:12]([CH3:14])[CH3:13])(=[O:19])[CH3:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 178165293-Hydroxy-4-isobutoxybenzaldehyde

Product 1

HCID 178165465-Formyl-2-isobutoxyphenyl acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In 31 ml of N,N-dimethylformamide are suspended 3.1 g of 3-hydroxy-4-isobutoxybenzaldehyde, 0.7 g of 60% sodium hydride and 3 ml of acetic anhydride. The suspension is stirred for 2 hours at 100° C. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. Thus, 4.2 g of 5-formyl-2-isobutoxyphenyl acetate is obtained as a yellow oily product.

Workup

  1. customthe organic layer is separated
  2. customThe organic layer thus obtained
  3. washis washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-92a1428cc0b84526b92e2f17daafb34e
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

Loading…