Hydrochloric Acid → 4-Formyl-3-hydroxyphenyl acetate

HRID 2369828Notes

Reaction equation

HRID 2369828 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[C:7]([O:13]C(=O)C)[CH:6]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C.O.C(OCC)(=O)C>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[O:12])=[C:7]([OH:13])[CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11127858HCID 11127858, compound

Product 1

HCID 126480914-Formyl-3-hydroxyphenyl acetateYield 44.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-formylbenzene-1,3-diyl diacetate (5.56 g, 25.08 mmol) in ethanol (20 mL) was added a solution of sodium hydroxide (1.00 g, 25.08 mmol) in water (12 mL). The reaction was stirred overnight at room temperature. The reaction was carefully neutralized with 2.0 N aqueous solution of hydrochloric acid (12.8 mL) at 0° C. and diluted with ethyl acetate (400 mL). The organic layer was washed with water (60 mL) and saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford, the product (2.01 g, 44% yield) as a gray solid: 1H NMR (400 MHz, d-MeOH): δ 9.90 (s, 1H), 7.68 (d, 1H), 6.80 (d, 1H), 6.75 (s, 1H), 4.82 (br s, 1H), 2.20 (s, 3H).

Workup

  1. washThe organic layer was washed with water (60 mL) and saturated aqueous sodium chloride (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford

Sources & evidence

ORD record
ord-2c2c921313354294946711a8f50c7eb3
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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