Cyclohex-2-ene-1,2-dicarboxylic acid → 3a,4,5,6-Tetrahydro-2-benzofuran-1,3-dione

HRID 329560Notes

Reaction equation

HRID 329560 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([OH:9])=O)[C:2]=1[C:10]([OH:12])=[O:11]>C(OC(=O)C)(=O)C.C(O)(=O)C>[C:10]1(=[O:11])[O:12][C:7](=[O:9])[CH:3]2[CH2:4][CH2:5][CH2:6][CH:1]=[C:2]12

Participants

4

Reactant 1

HCID 15051956Cyclohex-2-ene-1,2-dicarboxylic acid

Product 1

HCID 133216383a,4,5,6-Tetrahydro-2-benzofuran-1,3-dioneYield 49.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A stirred solution of 5.0 grams (0.029 mole) of cyclohexene-2,3-dicarboxylic acid in 30 ml of acetic anhydride and 100 ml of acetic acid was heated under reflux for four hours. The reaction mixture was concentrated under reduced pressure to a residual oil. The oil was washed with petroleum ether and evacuated under high vacuum to yield 2.2 grams of 2,3,4,5-tetrahydrophthalic anhydride as a semi-solid.

Workup

  1. temperatureunder reflux for four hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure to a residual oil
  3. washThe oil was washed with petroleum ether
  4. customevacuated under high vacuum

Sources & evidence

ORD record
ord-8cc0fc8a0ee74fc68dc6fbe955e72b1f
Source dataset
uspto-grants-1990_01
Patent number
US04892578

Reaction notes

Loading…