Benzene → HCID 53657641, compound

HRID 328750Notes

Reaction equation

HRID 328750 reaction equation
[CH:1]1CCCC=1.C1C=CC=CC=1.S([O-])([O-])(=O)=O.[Ba+2].[C:18]([CH:22]1[C:26](=[O:27])[CH2:25][CH:24]([O:28][C:29](=[O:31])[CH3:30])[CH:23]1[CH2:32][C:33]([OH:35])=[O:34])([O:20][CH3:21])=[O:19]>C(Cl)(Cl)Cl>[CH3:1][O:34][C:33](=[O:35])[CH2:32][CH:23]1[CH:24]([O:28][C:29](=[O:31])[CH3:30])[CH2:25][C:26](=[O:27])[CH:22]1[C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 241BenzeneHCID 8882CyclopenteneHCID 24414Barium SulfateHCID 21440264HCID 21440264, compound

Product 1

HCID 53657641HCID 53657641, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The cyclopentene acid, V, (9.5 g.) is dissolved in 180 ml. of benzene and the solution is hydrogenated at room temperature and atmospheric pressure in the presence of 0.5 g. of palladiated barium sulfate. When the theoretical amount of hydrogen is absorbed, catalyst is filtered off and the solution is evaporated to dryness under vacuum, yielding 9 g. (95%) of the methy ester of 2-carbomethoxy-3-oxo-5-acetoxycyclopentaneacetic acid with the required stereochemical configuration. The compound is a rather unstable solid, melting at 54° C; [α]d25 :- 17.8 (C=1.017% in CHCl3).

Workup

  1. customis hydrogenated at room temperature
  2. customWhen the theoretical amount of hydrogen is absorbed
  3. filtrationcatalyst is filtered off
  4. customthe solution is evaporated to dryness under vacuum
  5. customyielding 9 g

Sources & evidence

ORD record
ord-2e32adca036540748f87fb58504309fa
Source dataset
uspto-grants-1977_04
Patent number
US04018797

Reaction notes

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