3-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl- → 4-(2,2,3-Trimethylcyclopentyl)butanoic acid

HRID 1957880Notes

Reaction equation

HRID 1957880 reaction equation
[CH3:1][C:2]1([CH3:11])[C:6]([CH3:7])=[CH:5][CH2:4][CH:3]1[CH2:8][CH:9]=O.[CH3:12][C:13]1([CH3:27])[C:17]([CH3:18])=[CH:16][CH2:15][CH:14]1[CH2:19][CH:20]=[CH:21][C:22]([O:24]CC)=[O:23]>>[CH3:27][C:13]1([CH3:12])[CH:17]([CH3:18])[CH2:16][CH2:15][CH:14]1[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23].[CH2:20]([CH:21]([CH2:9][CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]([CH3:7])[C:2]1([CH3:11])[CH3:1])[C:22]([OH:24])=[O:23])[CH3:19]

Participants

4

Reactant 2

HCID 984973-Cyclopentene-1-acetaldehyde, 2,2,3-trimethyl-HCID 67506229HCID 67506229, compound

Product 2

HCID 250998174-(2,2,3-Trimethylcyclopentyl)butanoic acidHCID 67505738HCID 67505738, compound

Procedure

4-(2,2,3-trimethylcyclopentyl)butanoic acid was synthesized in three steps; the first step reacts 2-(2,2,3-trimethylcyclopent-3-en-1-yl)acetaldehyde (aka campholenic aldehyde) to ethyl 4-(2,2,3-trimethylcyclopent-3-enyl)but-2-enoate, in the second step the latter was subjected to a hydrogenation procedure to form ethyl 4-(2,2,3-trimethylcyclopentyl)butanoic acid, and in the third step, from the latter, 4-(2,2,3-trimethylcyclopentyl)butanoic acid was formed in presence of sodium hydroxide (NaOH) and tetrahydrofuran (THF).

Sources & evidence

ORD record
ord-4b755ff78fd94955878c338a70209332
Source dataset
uspto-grants-2013_04
Patent number
US08409649B2

Reaction notes

Loading…