Hydrochloric Acid → 5-formyl-2-hydroxyphenyl acetate

HRID 2070600Notes

Reaction equation

HRID 2070600 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[H-].[Na+].[C:13](OC(=O)C)(=[O:15])[CH3:14].Cl>CN(C)C=O>[CH:5]([C:4]1[CH:7]=[CH:8][C:9]([OH:10])=[C:2]([O:1][C:13](=[O:15])[CH3:14])[CH:3]=1)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 87683,4-DihydroxybenzaldehydeHCID 24758Sodium hydride

Product 1

HCID 2623445-formyl-2-hydroxyphenyl acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,4-dihydroxybenzaldehyde (5.0 g) in N,N-dimethylformamide (36 mL) was added 60% sodium hydride (1.45 g) under ice-cooling, followed by stirring the reaction mixture at room temperature for 10 minutes. Then, after addition of acetic anhydride (3.6 mL), the reaction mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 2N aqueous hydrochloric acid solution under ice-cooling, followed by extraction with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:2 to 1:1) to give acetic acid 5-formyl-2-hydroxyphenyl ester (4.9 g).

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at room temperature for 1 hour
  3. temperaturecooling
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:2 to 1:1)

Sources & evidence

ORD record
ord-dd388fedf1f441a08af19b7399bceb7a
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

Loading…