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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 279903
Notes
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Reaction equation

HRID 279903 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-dac1fdd7f9ce4f17923eacf77786b5cc
Source dataset
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04587234

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes