Sodium Hydroxide → HCID 86732967, compound
Reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[CH:10]1[CH:14]([OH:15])[CH:13]=[CH:12][C:11]1=O)([OH:3])=[O:2].[OH-:17].[Na+]>>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7]/[CH:8]=[CH:9]\[C:10]1[C:14](=[O:15])[CH2:13][CH:12]([OH:17])[CH:11]=1)([OH:3])=[O:2]Participants
3
Procedure
A solution of 1.0 mmole of all-cis-2-(6-carboxy-2-cis-hexenyl)-3,4-oxidocyclopentanone (Example 1106) and 3.0 mmoles of sodium carbonate in 15 ml. of water is allowed to stand at room temperature for 3 hours. The solution is acidified with HCl, saturated with sodium chloride, and extracted with ether. The extract is washed with brine, dried over magnesium sulfate, and concentrated to give a mixture of the title compound and the isomeric compound, 2-(6-carboxy-2-cis-hexenyl)-3-hydroxycyclopent-4-en-1-one. Further treatment of this mixture with N/10 sodium hydroxide at room temperatue for 30 minutes causes the rearrangement of the latter isomer to the title compound, which is isolated from basic solution as above.
Sources & evidence
- ORD record
- ord-bee5e146c43049febef17ef48abe3178
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04439365
Reaction notes
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