Methanol → Methyl (3-cyano-4,5-dihydroxyphenyl)glyoxylate

HRID 2260276Notes

Reaction equation

HRID 2260276 reaction equation
B(Br)(Br)Br.[C:5]([C:7]1[CH:8]=[C:9]([C:17](=[O:27])[C:18]([O:20][CH2:21]CCCCC)=[O:19])[CH:10]=[C:11]([O:15]C)[C:12]=1[O:13]C)#[N:6].CO>C(Cl)Cl>[C:5]([C:7]1[CH:8]=[C:9]([C:17](=[O:27])[C:18]([O:20][CH3:21])=[O:19])[CH:10]=[C:11]([OH:15])[C:12]=1[OH:13])#[N:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 17977685Hexyl (3-cyano-4,5-dimethoxyphenyl)glyoxylate

Product 1

HCID 14451002Methyl (3-cyano-4,5-dihydroxyphenyl)glyoxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.8 ml of boron tribromide dissolved in 20 ml of methylene chloride are added dropwise while cooling with ice within 20 minutes to 4.0 g of hexyl (3-cyano-4,5-dimethoxyphenyl)glyoxylate dissolved in 100 ml of methylene chloride and the reaction mixture is stirred at room temperature for 18 hours, 40 ml of methanol are subsequently added dropwise thereto at -60°, the mixture is stirred at room temperature for 1 hour and evaporated. The residue is taken up in methanol. It is heated under reflux for 10 minutes, evaporated to dryness and dried in a high vacuum. The thus-obtained crude product is recrystallized from acetonitrile. There is obtained methyl (3-cyano-4,5-dihydroxyphenyl)glyoxylate of m.p. 252°.

Workup

  1. additionare added dropwise
  2. stirringat -60°, the mixture is stirred at room temperature for 1 hour
  3. customevaporated
  4. temperatureIt is heated
  5. temperatureunder reflux for 10 minutes
  6. customevaporated to dryness
  7. customdried in a high vacuum
  8. customThe thus-obtained crude product
  9. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-dd36f9cbdc83435c854635cd942ebc60
Source dataset
uspto-grants-1995_12
Patent number
US05476875

Reaction notes

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