Sodium Hydroxide → 2-(6-Carboxy-2-cis-hexenyl)cyclopent-2-en-1-one

HRID 1730663Notes

Reaction equation

HRID 1730663 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH:10]1[CH:14]=[CH:13][CH2:12][C:11]1=[O:15])([OH:3])=[O:2].[OH-].[Na+]>>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)([OH:3])=[O:2]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 867329692-(6-Carboxy-2-cis-hexenyl)cyclopent-3-en-1-one

Product 1

HCID 867329642-(6-Carboxy-2-cis-hexenyl)cyclopent-2-en-1-one

Procedure

A solution of 3 g. of crude 2-(6-carboxy-2-cis-hexenyl)cyclopent-3-en-1-one (Example 17) in 100 ml. of 2% sodium hydroxide is stirred at 80° C. under nitrogen for 1.5 hours. The cooled solution is acidified to Congo Red and extracted with ether. The ethereal extracts are dried over sodium sulfate and evaporated at reduced pressure to afford the product.

Workup

  1. extractionextracted with ether
  2. dry with materialThe ethereal extracts are dried over sodium sulfate
  3. customevaporated at reduced pressure
  4. customto afford the product

Sources & evidence

ORD record
ord-34fb04372f9d48ee8233451a0420910b
Source dataset
uspto-grants-1976_11
Patent number
US03993674

Reaction notes

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