Carbon Dioxide → HCID 58232275, compound

HRID 1618344Notes

Reaction equation

HRID 1618344 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(C[C:11]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[CH:15][CH:14]=[C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])C=1CC(O)=O)(O)=O.[C:35](=[O:37])=O.C([O:41][CH2:42][CH3:43])(=O)C>C1COCC1>[OH:41][CH2:42][C:43]1[C:13]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])=[CH:14][CH:15]=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[C:11]=1[CH2:35][OH:37]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8857Ethyl Acetate2×HCID 21226445Aluminium lithium hydride2×HCID 67087804HCID 67087804, compound

Product 1

HCID 58232275HCID 58232275, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

250 ml of THF are slowly added to 10.13 g (267.3 mmol) of lithium aluminium hydride, then 71.5 g (190.9 mmol) of 1,2-dicarboxymethyl-3,6-di-o-tolylbenzene, dissolved in 450 ml of THF, are slowly added at such a rate that the temperature does not rise above 40° C. If necessary, the mixture is cooled using dry ice. When the addition is complete, the suspension is heated under reflux for 2 h. When the conversion is complete, a mixture of 120 ml of ethyl acetate and 340 ml of THF is slowly added with cooling at 0° C. (reaction of the excess lithium aluminium hydride with ethyl acetate). When quenching is complete, 300 ml of ethanol are carefully added, and the mixture is subjected to aqueous work-up. 200 ml of water are added, the precipitate is filtered off with suction, and the mother liquor is evaporated a little, extracted with ethyl acetate and dichloromethane, dried over MgSO4 and evaporated, giving 61 g of crude product, which can be employed directly in the next transformation.

Workup

  1. additionare slowly added at such a rate that the temperature
  2. customdoes not rise above 40° C
  3. temperatureIf necessary, the mixture is cooled
  4. additionWhen the addition
  5. temperaturethe suspension is heated
  6. temperatureunder reflux for 2 h
  7. additionis slowly added
  8. customWhen quenching
  9. addition300 ml of ethanol are carefully added
  10. addition200 ml of water are added
  11. filtrationthe precipitate is filtered off with suction
  12. customthe mother liquor is evaporated a little,
  13. extractionextracted with ethyl acetate and dichloromethane
  14. dry with materialdried over MgSO4
  15. customevaporated

Sources & evidence

ORD record
ord-4fde9edb49f04258b0cf230ce9d3c998
Source dataset
uspto-grants-2014_07
Patent number
US08766001B2

Reaction notes

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