Hydrochloric Acid → DIETHYL BENZYLSUCCINATE

HRID 483382Notes

Reaction equation

HRID 483382 reaction equation
[C:1]1([CH2:7][C:8](C(OCC)=O)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>>[C:1]1([CH2:7][CH:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 563419Triethyl 3-phenyl-1,2,2-propanetricarboxylate

Product 1

HCID 576172DIETHYL BENZYLSUCCINATEYield 84.7%

Procedure

A solution of the product from step (a) (23.6 g) in c.HCl (326 ml) was stirred under reflux for 46 hours, then cooled. The resulting precipitate was extracted with chloroform (×3) and the extracts combined, washed with 2M aqu. KOH (×2), acidified to pH 4.0 (2M aqu. HCl) and cooled. The resulting precipitate was filtered off, washed with water and dried in vacuo to give the desired product (15.7 g). The 200 MHz 1H NMR was consistent with the proposed structure.

Workup

  1. temperatureunder reflux for 46 hours
  2. temperaturecooled
  3. extractionThe resulting precipitate was extracted with chloroform (×3)
  4. washwashed with 2M aqu
  5. temperaturecooled
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-bc07f67c065949cfb8820a459ba7ce85
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

Loading…