Cyclopentadiene → 2-Hydroxybicyclo(2.2.1)heptane-2-carboxylic acid
Reaction equation
C=C1OCOC1=O.C1CC=CC=1.[OH:13][C:14]1([C:21]([OH:23])=[O:22])[CH2:19][CH:18]2[CH2:20][C:15]1=[CH:16][CH2:17]2>>[OH:13][C:14]1([C:21]([OH:23])=[O:22])[CH2:19][CH:18]2[CH2:20][CH:15]1[CH2:16][CH2:17]2Participants
4
Procedure
An optically active 5-methylenedioxolan-4-one derivative is subjected to Diels-Alder reaction with cyclopentadiene, and the resulting Diels-Alder reaction product is hydrolyzed to convert it into an optically active 2-hydroxynorbornene-2-carboxylic acid, which is then subjected to catalytic hydrogenation to form an optically active 2-hydroxynorbornane-2-carboxylic acid. The hydroxycarboxylic acid is subjected to oxidative decarboxylation to obtain an optically active 2-norbornanone.
Workup
- customthe resulting Diels-Alder reaction product
Sources & evidence
- ORD record
- ord-3a844c17f954450db1de2ea97a7c7f78
- Source dataset
- uspto-grants-1996_03
- Patent number
- US05498799
Reaction notes
Loading…