Hydroquinone → HCID 67908432, compound

HRID 542613Notes

Reaction equation

HRID 542613 reaction equation
[OH:1][CH:2]1[O:6][C:5](=[O:7])[CH:4]=[CH:3]1.[C:8]1([CH:15]=[CH:14][C:12](O)=[CH:11]C=1)O.C1CC=CC=1>C(Cl)(Cl)Cl>[OH:7][CH:5]1[CH:4]2[C:3](=[C:11]3[CH2:12][CH:14]2[CH2:15][CH2:8]3)[C:2](=[O:1])[O:6]1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 7612CyclopentadieneHCID 210765-Hydroxyfuran-2(5H)-one

Product 1

HCID 67908432HCID 67908432, compoundYield 61,756.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 30 g of 5-hydroxy-2(5H)-furanone, 150 ml of chloroform, 50 mg of hydroquinone and 35 ml of freshly distilled cyclopentadiene was stirred at 20° C. under an inert atmosphere and stirred for 17 hours at 20°-45° C. The mixture was evaporated to dryness under reduced pressure and the residue was crystallized from an isopropyl ether-petroleum ether mixture to obtain 46.6 g of 3-hydroxy-tetrahydro-4,7-methano-isobenzofuran-1-one melting at ≃103° C.

Workup

  1. stirringstirred for 17 hours at 20°-45° C
  2. customThe mixture was evaporated to dryness under reduced pressure
  3. customthe residue was crystallized from an isopropyl ether-petroleum ether mixture

Sources & evidence

ORD record
ord-713d9d179c834a88884167e9389b3622
Source dataset
uspto-grants-1987_04
Patent number
US04658043

Reaction notes

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