Diethyl 3,3'-(1,4-phenylene)dipropanoate → HCID 19907404, compound

HRID 2371548Notes

Reaction equation

HRID 2371548 reaction equation
C([O:3][C:4]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](OCC)=[O:17])=[CH:10][CH:9]=1)=O)C.C(=O)=O.CC(C)=O.[H-].C([NH2+]CC(C)C)C(C)C>C1(C)C=CC=CC=1.C(O)C.O>[CH:16]([CH2:15][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][CH:4]=[O:3])=[CH:13][CH:12]=1)=[O:17]

Participants

7

Reactant 3

HCID 12169277Diethyl 3,3'-(1,4-phenylene)dipropanoateHCID 18522661Acetone cardiceHCID 21898182Diisobutylammonium hydride

Product 1

HCID 19907404HCID 19907404, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent3×HCID 962WaterSolventHCID 1140TolueneSolvent3×

Procedure

First, 2.78 g of 1,4-bis(2-ethoxycarbonylethyl)benzene was dissolved in 40 ml of absolute toluene, the solution was cooled to -65° C. with dry ice/acetone, and a solution of 1M diisobutylammonium hydride in 24 ml of toluene was added dropwise with stirring over 25 minutes, and the mixture was further stirred at -70° C. for 2 hours. Next, 2.5 ml of ethanol/2.5 ml of toluene, 3 ml of ethanol, and 2.75 ml of water/5.5 ml of ethanol were added dropwise in this order, and after removing cooling bath, the mixture was allowed to warm to a room temperature with stirring. After adding 10 ml of water, the mixture was adjusted to a pH value of not more than 3 with 6N hydrochloric acid. The organic layer was separated, washed with water and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and evaporated under a reduced pressure. The residue was applied to a silica gel column and eluted with hexane/ethyl acetate (6:1) to obtain 988 mg of 1,4-bis(2-formylethyl)benzene as a colorless crystal.

Workup

  1. stirringthe mixture was further stirred at -70° C. for 2 hours
  2. customafter removing
  3. temperaturecooling bath
  4. stirringwith stirring
  5. additionAfter adding 10 ml of water
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materiala saturated sodium chloride aqueous solution, dried over magnesium sulfate
  9. customevaporated under a reduced pressure
  10. washeluted with hexane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-78c9febb83c545ccba52f998d4e0a881
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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