4-Hydroxybenzaldehyde → 4-Hydroxybenzoic Acid

HRID 1006313Notes

Reaction equation

HRID 1006313 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH:11][C:12]1[CH:19]=[CH:18][C:15](C=O)=[CH:14][CH:13]=1.OOS([O-])=O.[K+].CC[O:28][C:29](C)=[O:30]>CN(C=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH:29]([O:30][C:15]1[CH:14]=[CH:13][C:12]([OH:11])=[CH:19][CH:18]=1)=[O:28]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 1354-Hydroxybenzoic AcidHCID 8857Ethyl AcetateHCID 23707502Potassium hydroxy sulfite

Product 2

HCID 1354-Hydroxybenzoic AcidHCID 13148437HCID 13148437, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To prepare 4-hydroxy benzoic acid, 4-hydroxybenzaldehyde (100 mg) was dissolved in DMF (10 mL), and OXONE (0.503 g) was added and stirred at room temperature for 18 hours with the reaction having a final volume (11 mL). The reaction was monitored by TLC or GC analysis. EtOAc was added to extract the products and 1N HCl was used to dissolve the salts. The organic extract was washed with 1N HCl (30 mL×3) and brine (30 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 4-hydroxy benzoic acid in 19% yield and 4-hydroxyphenol formate in 62% yield after purification by silica gel column chromatography. 4-Hydroxyphenyl Formate: 1H NMR (CDCl3, 300 MHz): δ8.27 (s, 1H), 6.98(d, 2H, J=9.0), 6.78 (d, 2H,J=8.9), 5.35 (bs, 1H).

Workup

  1. extractionto extract the products and 1N HCl
  2. dissolutionto dissolve the salts
  3. extractionThe organic extract
  4. washwas washed with 1N HCl (30 mL×3) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5db398a221174f439752ee9ed61c13ba
Source dataset
uspto-grants-2004_09
Patent number
US06787671B2

Reaction notes

Loading…