4-Hydroxybenzaldehyde → Hydroquinone

HRID 1006311Notes

Reaction equation

HRID 1006311 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[OH:12][C:13]1[CH:20]=[CH:19][C:16](C=O)=[CH:15][CH:14]=1.[OH:21]OS([O-])=O.[K+].CCOC(C)=O>CO>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1.[OH:21][C:16]1[CH:19]=[CH:20][C:13]([OH:12])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 7456MethylparabenHCID 8857Ethyl AcetateHCID 23707502Potassium hydroxy sulfite

Product 2

HCID 785HydroquinoneHCID 7456Methylparaben

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To prepare methyl 4-hydroxybenzoate, 4-hydroxybenzaldehyde (100 mg) was dissolved in MeOH (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 methyl 4-hydroxybenzoate in 4% yield and 4-hydroxyphenol in 77% yield after purification by silica gel column chromatography.

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-5a005a0c2cf442778ecfedeae3cf0984
Source dataset
uspto-grants-2004_09
Patent number
US06787671B2

Reaction notes

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