Hydrogen Peroxide → 2-Methoxy-1,4-benzoquinone

HRID 231053

Reaction equation

HRID 231053 reaction equation
O=C[C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[OH-].[Na+].OO.I([O-])(=O)(=O)=[O:17].[Na+]>O.C(O)(=O)C>[CH3:7][O:6][C:5]1[C:8](=[O:9])[CH:10]=[CH:11][C:3](=[O:17])[CH:4]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1183VanillinHCID 14798Sodium HydroxideHCID 23667635Sodium periodate

Product 1

HCID 761462-Methoxy-1,4-benzoquinoneYield 334.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
10 °C

Procedure

Vanillin (2.432 kg) was added to a solution of sodium hydroxide (640 g) in water (8 l) and cooled to 10° C. with an ice-bath. Then a solution of hydrogen peroxide (30%) (2.4 1) was added at a rate to keep the temperature of the reacting mixture below 30° C. The addition completed (about 2 hours), the reaction mixture was added over a period of 3 hours to a suspension of sodium periodate (880 g) in water (4 l) and acetic acid (640 ml) cooled with an ice-bath to 10° C. (the temperature of the reacting mixture was kept below 35° C.). The resulting precipitate was filtered, washed with cold water followed by ethanol/hexane (1:1) mixture and air-dried to afford the title compound (1.9 kg), m.p. 144°-147° C.

Workup

  1. customthe temperature of the reacting mixture below 30° C
  2. additionThe addition
  3. custom(about 2 hours)
  4. temperaturecooled with an ice-bath to 10° C. (the temperature of the reacting mixture
  5. customwas kept below 35° C.
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with cold water
  8. customair-dried

Sources & evidence

ORD record
ord-7cf5da72efb04cbab0849cda4ed81999
Source dataset
uspto-grants-1989_07
Patent number
US04845083

Linked notes

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