Sodium Hydroxide → HCID 13218156, compound

HRID 847139Notes

Reaction equation

HRID 847139 reaction equation
[C:1]([C@@H:5]1[CH2:9][C:8](=[CH2:10])[CH2:7][C@H:6]1[C:11]([O:13]C)=[O:12])([O:3]C)=[O:2].[OH-].[Na+]>>[CH2:10]=[C:8]1[CH2:7][C@@H:6]([C:11]([OH:13])=[O:12])[C@H:5]([C:1]([OH:3])=[O:2])[CH2:9]1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 642644HCID 642644, compound

Product 1

HCID 13218156HCID 13218156, compoundYield 77.7%

Procedure

A diester, trans-1,2-di-carbomethoxy-4-methylenecyclopentane, 1 (1.48g, 7.47 mmol) prepared by the method of Trost (J. Am. Chem. Soc. 105 2315 (1983) was heated under reflux for 2 hours with 2N sodium hydroxide (11 ml, 22 mmol). The resulting solution was cooled in an ice bath and acidified with concentrated (37%) hydrochloric acid (8.0 ml) until a pH of 0.6 was attained. .The resulting slurry was filtered, washed with water, and dried in vacuo to give the diacid 2 (0.987g, 77.7%) as a colorless powder: mp 178°-179° C.; Anal. calcd for C8H10O4 : C, 56.47; H, 5.92. Found: C, 56.08; H, 5.87.

Workup

  1. temperature105 2315 (1983) was heated
  2. temperatureThe resulting solution was cooled in an ice bath
  3. concentrationwith concentrated (37%) hydrochloric acid (8.0 ml) until a pH of 0.6
  4. filtration.The resulting slurry was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1906462807cf4a729b4d8663d57253da
Source dataset
uspto-grants-1992_08
Patent number
US05140023

Reaction notes

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