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5,6,7,8-tetrahydro-1H-cyclohepta[c]furan-1,3(4H)-dione → rac-(3aR,8aS)-hexahydro-1H-cyclohepta(c)furan-1,3(3aH)-dione

HRID 235917
Notes
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Reaction equation

HRID 235917 reaction equation
[C:1]12[C:11](=[O:12])[O:10][C:8](=[O:9])[C:2]=1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]2>C(OC(=O)C)(=O)C>[C@@H:2]12[C:8](=[O:9])[O:10][C:11](=[O:12])[C@@H:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 136137545,6,7,8-tetrahydro-1H-cyclohepta[c]furan-1,3(4H)-dione

Product 1

HCID 54300481rac-(3aR,8aS)-hexahydro-1H-cyclohepta(c)furan-1,3(3aH)-dione

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Hydrogenation of this anhydride using platinic oxide in acetic anhydride according to the procedure set forth in Coll. Czech. Chem. Comm., Vol. 26, p. 262 (1961) yields (cis)-1,2-cycloheptanedicarboxylic anhydride. Treatment with water and recrystallization gives (cis)-1,2-cycloheptanedicarboxylic acid.

Sources & evidence

ORD record
ord-f914d0f0eb2c4d2586a11ab419cc79e7
Source dataset
uspto-grants-1987_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04642315

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes