Sodium Chloride → HCID 11063353, compound

HRID 1283509Notes

Reaction equation

HRID 1283509 reaction equation
C[O:2][C:3]1[CH:9]=[CH:8]C(O)=[CH:5][CH:4]=1.[CH3:10][CH:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17].C(C(CC)=O)=C.[Cl-].[Na+]>C1C=CC=CC=1.O.C(O)(=O)C>[CH3:10][C:11]1([CH2:5][CH2:4][C:3](=[O:2])[CH2:9][CH3:8])[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 90154-MethoxyphenolHCID 130052-Methyl-1,3-cyclopentanedioneHCID 153941-Penten-3-one2×

Product 1

HCID 11063353HCID 11063353, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A total of 88 mg. of hydroquinone monomethyl ether was added to 10 ml. of ether vinyl ketone to stabilize the latter compound. There was then added to the above mixture 0.08 ml. of glacial acetic acid, 26 ml. of dimeneralized water and 11.2 g. of 2-methyl-1,3-cyclopentanedione. The resulting mixture was stirred under argon at room temperature for 15 days. An additional 9 ml. of ethyl vinyl ketone was added at the fourth day and 9.5 ml. of ethyl vinyl ketone was added at the ninth day. After 15 days, 50 ml. of benzene was added and sufficient sodium chloride was added to the aqueous phase to allow separation after shaking. The phases were separated and the aqueous phase re-extracted with 50 ml. of benzene. The combined benzene extracts were treated with a mixture of sodium sulfate, magnesium sulfate and activated charcoal. The solids were filtered off and were washed with a mixture of chloroform and ether. The combined filtrates were evaporated in vacuo and the residue was treated with an additional portion of benzene followed by concentration to dryness in vacuo. There was obtained 21.1 g. of an oil residue which was fractionally distilled at 0.05 mmHg and the fraction boiling in the range of 105°-118°C. was collected; yield 17.47 g. (89 percent). This fraction was redistilled at 0.025 mmHg to give a fraction boiling at 97°-115°C.; yield 16 g. (83.5 percent) of the above-captioned product.

Workup

  1. waitAfter 15 days
  2. customseparation
  3. stirringafter shaking
  4. customThe phases were separated
  5. extractionthe aqueous phase re-extracted with 50 ml
  6. additionThe combined benzene extracts were treated with a mixture of sodium sulfate, magnesium sulfate and activated charcoal
  7. filtrationThe solids were filtered off
  8. washwere washed with a mixture of chloroform and ether
  9. customThe combined filtrates were evaporated in vacuo
  10. additionthe residue was treated with an additional portion of benzene
  11. concentrationfollowed by concentration to dryness in vacuo
  12. customThere was obtained 21.1 g
  13. distillationof an oil residue which was fractionally distilled at 0.05 mmHg
  14. customboiling in the range of 105°-118°C.
  15. customwas collected
  16. distillationThis fraction was redistilled at 0.025 mmHg
  17. customto give a fraction boiling at 97°-115°C.

Sources & evidence

ORD record
ord-b41ac37967144760992ba8a5d46045fe
Source dataset
uspto-grants-1976_08
Patent number
US03975442

Reaction notes

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