Acetic Acid → HCID 54162586, compound

HRID 851323Notes

Reaction equation

HRID 851323 reaction equation
[OH-].[K+].[CH3:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[O:5].[CH:14](=O)[CH:15]([CH3:17])[CH3:16].C(O)(=O)C>O.CO>[CH3:14][CH:15]([CH:17]=[CH:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)[CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6561IsobutyraldehydeHCID 74764'-MethoxyacetophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 54162586HCID 54162586, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

17 g of potassium hydroxide were dissolved in 125 ml of water and 125 ml of methanol, and 150 g of 4-methoxyacetophenone were added. 80 g of isobutyraldehyde were added dropwise (in the course of 1.5 hours) at 50° C. After 3.5 hours, the mixture was cooled to room temperature and neutralized with acetic acid (about 20 ml). The dimeric condensation product was filtered off, washed with methanol and dried in air. Yield: 175 g. The solid was mixed with 5 g of sodium acetate and the mixture was distilled under a waterpump vacuum. 165 g of a yellow oil which solidified at room temperature and was a mixture of 2-methyl-5-oxo-5-(4'-methoxyphenyl)-2-pentene and 2-methyl-5-oxo-5-(4'-methoxyphenyl)-3-pentene were obtained. Boiling point of the isomer mixture=158°-165° C./17 mbars.

Workup

  1. filtrationThe dimeric condensation product was filtered off
  2. washwashed with methanol
  3. customdried in air
  4. additionThe solid was mixed with 5 g of sodium acetate
  5. distillationthe mixture was distilled under a waterpump vacuum
  6. customsolidified at room temperature
  7. additiona mixture of 2-methyl-5-oxo-5-(4'-methoxyphenyl)-2-pentene

Sources & evidence

ORD record
ord-bd87cb485d434d109b3a837e8a6b2f54
Source dataset
uspto-grants-1983_05
Patent number
US04384114

Reaction notes

Loading…