Tetrahydrofuran → Phthalide

HRID 1763860Notes

Reaction equation

HRID 1763860 reaction equation
Cl[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[O:3]1.O1CCCC1>[Ni].C(N(CC)CC)C>[C:4]1([C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][O:3]1)=[O:5]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 954693-Chlorophthalide

Product 1

HCID 6885PhthalideYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
65 °C

Procedure

A 1-liter lift magnet autoclave is charged with 110 g of 3-chlorophthalide, 10 g of nickel catalyst RCH 55/10 (commercial product of Farbwerke Hoechst AG) and 400 ml of tetrahydrofuran to which 66 g of triethylamine is added. After purging the air with nitrogen, hydrogen is pumped in to a pressure of 10 bars, and the temperature is raised, with stirring, to 65° C. The hydrogen consumption is compensated by additions in the range between 10 and 20 bars for a period of 41/2 hours. After the absorption of hydrogen ceases, the catalyst and precipitated salt are filtered out and the solvent is withdrawn. After distillation of the residue between 88° and 90° C. and 0.2 Torr, 77.5 g of phthalide is obtained, of a melting point of 71° C. (gas-chromatographic analysis 98.95%).

Workup

  1. additionis added
  2. customAfter purging the air with nitrogen, hydrogen
  3. temperaturethe temperature is raised
  4. customThe hydrogen consumption
  5. customAfter the absorption of hydrogen ceases
  6. customthe catalyst and precipitated salt
  7. filtrationare filtered out
  8. customthe solvent is withdrawn
  9. distillationAfter distillation of the residue between 88° and 90° C. and 0.2 Torr

Sources & evidence

ORD record
ord-90dc5f675c134927943a8a045da7c888
Source dataset
uspto-grants-1978_09
Patent number
US04113741

Reaction notes

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