Hydroquinone → HCID 70363015, compound

HRID 1110331Notes

Reaction equation

HRID 1110331 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]=[C:3]2[C:7](=[O:10])[S:8][CH2:9][CH:2]12.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C1(C=CC(O)=CC=1)O.O=O>C1C=CC=CC=1.O>[O:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7](=[O:10])[S:8][CH2:9][CH:2]12

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 977OxygenHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 70362789HCID 70362789, compound

Product 1

HCID 70363015HCID 70363015, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A magnetically-stirred solution of 3,5,6,7-tetrahydro-1H-thieno[3,4-b]pyran-5-one (14.32 g, 0.09168 mol) in benzene (150 mL) was treated, in portions, with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (21.29 g, 0.09378 mol). The DDQ dissolved exothermically, giving a dark brown solution which gradually faded to orange, as the crystalline hydroquinone separated. The solids were removed by filtration and rinsed with CH2Cl2. The filtrates were concentrated in vacuo, and the residue was twice distilled (Kugelrohr) to give a mobile light orange oil. (bp>141° C./1.8 Torr or 126°-145° C./0.55 Torr, external temperature). Yield: 11.98 g (84.7%). The product solidified upon storage under N2 at -20° C. NMR and GC/MS data were in agreement with the proposed structure. The compound is sensitive to water, oxygen and light.

Workup

  1. customgiving a dark brown solution which
  2. customseparated
  3. customThe solids were removed by filtration
  4. washrinsed with CH2Cl2
  5. concentrationThe filtrates were concentrated in vacuo
  6. distillationthe residue was twice distilled (Kugelrohr)
  7. customto give a mobile light orange oil
  8. custom(bp>141° C./1.8 Torr or 126°-145° C./0.55 Torr, external temperature)
  9. customsolidified upon storage under N2 at -20° C

Sources & evidence

ORD record
ord-559ddc634d454d1c83075c18d5c72cc2
Source dataset
uspto-grants-1990_12
Patent number
US04974609

Reaction notes

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