Benzene → HCID 15137040, compound

HRID 1111153Notes

Reaction equation

HRID 1111153 reaction equation
[CH3:1][C:2]1[C:3](=[O:9])[CH:4]=[CH:5][C:6](=[O:8])[CH:7]=1.C[O:11][C:12]1[CH2:17][CH2:16]C=[CH:14][CH:13]=1.Cl.[CH:19]1C=CC=CC=1>CO>[OH:8][C:6]1[C:5]([CH3:19])=[CH:4][C:3]2[O:9][C@H:14]3[CH2:13][C:12](=[O:11])[CH2:17][CH2:16][C@H:1]3[C:2]=2[CH:7]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 11122Methyl-1,4-benzoquinoneHCID 75098Cyclohexadiene, 1-methoxy-

Product 1

HCID 15137040HCID 15137040, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.57 g (5.0 mmol) of 2-methyl-1,4-benzoquinone and 1.10 g (10.0 mmol) of 1-methoxy-1,3-cylcohexadiene in 10 mL of benzene was heated at reflux for 2 h. The solution was concentrated in vacuo and the residue dried under high vacuum to afford a pale yellow oil. This material was dissolved in 15 mL of methanol and to that solution was added 1 mL of 2.0M HCl. The solution was stirred at room temperature for 6 hours, then was concentrated to about 5 mL volume. This was partitioned between ethyl acetate and water and the aqueous layer was washed with two portions of ethyl acetate. The organic extracts were sequentially washed with water and NaCl solution, combined, dried over magnesium sulfate, and concentrated. The residue was crystallized from ether-hexane to afford 0.452 g white crystals, 41%.

Workup

  1. temperatureat reflux for 2 h
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue dried under high vacuum
  4. customto afford a pale yellow oil
  5. concentrationwas concentrated to about 5 mL volume
  6. customThis was partitioned between ethyl acetate and water
  7. washthe aqueous layer was washed with two portions of ethyl acetate
  8. washThe organic extracts were sequentially washed with water and NaCl solution
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was crystallized from ether-hexane

Sources & evidence

ORD record
ord-f7c2ee56e5c64c56b333e7aff761c576
Source dataset
uspto-grants-1990_12
Patent number
US04978679

Reaction notes

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