Hydrochloric Acid → HCID 15137042, compound

HRID 1111154Notes

Reaction equation

HRID 1111154 reaction equation
[CH2:1]([C:4]1[C:5](=[O:11])[CH:6]=[CH:7][C:8](=[O:10])[CH:9]=1)[CH2:2][CH3:3].C[O:13][C:14]1[CH2:19][CH2:18][CH:17]=[CH:16][CH:15]=1.Cl>C1C=CC=CC=1.CO>[OH:11][C:5]1[C:4]([CH2:1][CH2:2][CH3:3])=[CH:9][C:8]2[O:10][C@H:16]3[CH2:15][C:14](=[O:13])[CH2:19][CH2:18][C@H:17]3[C:7]=2[CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 75098Cyclohexadiene, 1-methoxy-HCID 15137041HCID 15137041, compound

Product 1

HCID 15137042HCID 15137042, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

A solution of 1.08 g (7.2 mmol) of 2-propyl-1,4-benzoquinone and 2.20 g (20.0 mmol) of 1-methoxy-1,3-cylcohexadiene in 20 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 20 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 0.764 g white crystals, 43%.

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-77291825912d42fba42564044f20f11c
Source dataset
uspto-grants-1990_12
Patent number
US04978679

Reaction notes

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