Toluene → HCID 14446267, compound

HRID 486423Notes

Reaction equation

HRID 486423 reaction equation
Cl[CH2:2][C:3]1[C:4]([CH3:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:10](OCC)(=O)CC(C)=O.[C:19](=[O:22])([O-])[O-].[K+].[K+].[C:25]1([CH3:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH3:9][C:4]1[C:5]([CH:19]=[O:22])=[CH:6][C:7]2=[C:8]3[C:3]=1[CH2:2][CH2:31][C:25]3([CH3:26])[CH2:30][CH2:29][C:28]2([CH3:27])[CH3:10]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8868Ethyl AcetoacetateHCID 11093alpha-Chloro-o-xyleneHCID 11430Potassium Carbonate

Product 1

HCID 14446267HCID 14446267, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The starting material 1,2,6,7,8,8a-hexahydro-3,6,6,8a-tetramethyl-4-acenaphthylenecarbaldehyde is prepared by substantially following the procedures of Fehr et al., U.S. Pat. No. 5,162,588. Specifically, in a 2.5 liter flask equipped with a mechanical stirrer, a condenser, a thermometer and a nitrogen inlet, α-chloro-o-xylene (available from Fluka Chemical Corp., Ronkonkoma, N.Y., 140.6 g) is mixed with ethyl acetoacetate (130 g), a fine powder of potassium carbonate (414 g) and 800 ml of toluene. The mixture is heated to 100° C. for 20 h. After cooling, H2O is added (500 ml). The organic phase is washed with water and saturated NaCl, then dried over Na2SO4 and evaporated, resulting in a brown oil. The oil is distilled (120° C.-125° C./5.65 Pa) to yield ethyl-2-acetyl-3-(2-methyl-1-phenyl)propanoate.

Workup

  1. customSpecifically, in a 2.5 liter flask equipped with a mechanical stirrer, a condenser
  2. temperatureAfter cooling
  3. washThe organic phase is washed with water and saturated NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customresulting in a brown oil
  7. distillationThe oil is distilled (120° C.-125° C./5.65 Pa)

Sources & evidence

ORD record
ord-da25b9881297403f8168387f344fa941
Source dataset
uspto-grants-1994_03
Patent number
US05292719

Reaction notes

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