Acetic Acid → HCID 54106535, compound

HRID 371419Notes

Reaction equation

HRID 371419 reaction equation
[CH3:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=O)=[CH:4][CH:3]=1.[C:18]([O:24][CH3:25])(=[O:23])[CH2:19][C:20]([CH3:22])=[O:21].N1CCCCC1.C(O)(=O)C>C(O)(C)C>[C:20]([C:19](=[CH:10][C:9]1[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=1[O:7][CH2:6][C:5]1[CH:16]=[CH:17][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:18]([O:24][CH3:25])=[O:23])(=[O:21])[CH3:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7757Methyl acetoacetateHCID 8082PiperidineHCID 6933042-[(4-methylbenzyl)oxy]benzaldehyde

Product 1

HCID 54106535HCID 54106535, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
40 °C

Procedure

25 g (110.6 millimols) of 2-(4-methylbenzyloxy)-benzaldehyde were stirred with 11.9 ml (110.6 millimols) of methyl acetoacetate in 66 ml of isopropanol, and a freshly prepared solution of 0.64 ml of piperidine and 0.38 ml of glacial acetic acid in 5.5 ml of isopropanol was added. The mixture was stirred for 1 hour at 60° C. and for 4 hours at 40° C., and was cooled and concentrated. The residue from evaporation was dissolved in ether, and the solution was washed successively with approx. 100 ml of 1N hydrochloric acid, with two portions of water, with saturated sodium bicarbonate solution and again with two portions of water. The ether phase was dried, filtered and concentrated. 35.3 g (98.51% of theory) of a dark yellow oil were obtained, and the oil was reacted further in the crude form.

Workup

  1. temperaturewas cooled
  2. concentrationconcentrated
  3. customThe residue from evaporation
  4. dissolutionwas dissolved in ether
  5. washthe solution was washed successively with approx. 100 ml of 1N hydrochloric acid, with two portions of water, with saturated sodium bicarbonate solution and again with two portions of water
  6. dry with materialThe ether phase was dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custom35.3 g (98.51% of theory) of a dark yellow oil were obtained
  10. customthe oil was reacted further in the crude form

Sources & evidence

ORD record
ord-b9062448f74042daae58b47f4470955f
Source dataset
uspto-grants-1985_07
Patent number
US04532248

Reaction notes

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