Benzene → HCID 13671393, compound

HRID 1588148Notes

Reaction equation

HRID 1588148 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9]COC)[C:6]([O:13][CH3:14])=[C:5]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH3:25])[C:4]=1[O:26]COC.Cl.C1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(O)(C)C.O1CCCC1.CO.C(OCC)(=O)C.C1C=CC=CC=1>[CH3:14][O:13][C:6]1[C:7](=[O:9])[CH:8]=[C:3]([O:2][CH3:1])[C:4](=[O:26])[C:5]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

8

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 13671391HCID 13671391, compound

Product 1

HCID 13671393HCID 13671393, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 21583983Benzene ethyl acetateSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent2×

Procedure

500 Milligrams of 1,4-dimethoxy-2,5-bis(methoxymethoxy)-3-(Z-6-undecenyl)benzene was dissolved in 10 ml of a mixed solvent of isopropanol-tetrahydrofuran, and at room temperature, under nitrogen gas stream conditions, 2 ml of isopropanol-tetrahydrofuran (1:1) solution containing 20% of hydrogen chloride was added thereto and the whole mixture was stirred for 3 hours. The solvent was removed by evaporating under reduced pressure on a water bath at below 20° C. The residue obtained was further treated by evaporation under reduced pressure with adding 20 ml of benzene so as to remove hydrogen chloride. The residue obtained was dissolved in 20 ml of methanol, and a small amount of sodium hydrogen carbonate was added, and the mixture was stirred for 1 hour under oxygen gas stream conditions. The color of the reaction mixture turned yellow, and the solvent was removed by evaporation under reduced pressure. The residue obtained was treated by means of a separative silica gel thin layer chromatography (F254, thickness: 2 mm, developer: 10% ethyl acetate-benzene) to obtain 320 mg of 2,5-dimethoxy-3(Z-6-undecenyl)-1,4-benzoquinone. Yellow oily substance.

Workup

  1. additionwas added
  2. customThe solvent was removed
  3. customby evaporating under reduced pressure on a water bath at below 20° C
  4. customThe residue obtained
  5. additionwas further treated by evaporation under reduced pressure
  6. customto remove hydrogen chloride
  7. customThe residue obtained
  8. stirringthe mixture was stirred for 1 hour under oxygen gas stream conditions
  9. customthe solvent was removed by evaporation under reduced pressure
  10. customThe residue obtained

Sources & evidence

ORD record
ord-fe8555415e5f4911a012a28513e3392d
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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