Reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][O:2]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[H][H]>[Pd]>[CH3:1][C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:4][CH2:3][OH:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
1250 Grams of isochroman having the structure: ##STR63## 25 grams of 5% palladium-on-carbon and 12.5 grams of citric acid are placed in a 4-liter autoclave. The autoclave is sealed, heated to 150° C. and pressurized with hydrogen at 200 psig. After five hours, 12.5 grams of additional citric acid is added to the autoclave and the autoclave is resealed. The autoclave is then heated at a pressure of 200 psig and 150° C. for an additional three hours. At the end of this additional three hour period, the autoclave is opened, the contents filtered and the filtrate is distilled over 2 grams of calcium carbonate through a 24" Goodloe column yielding the following fractions:
Workup
- customThe autoclave is sealed
- temperatureThe autoclave is then heated at a pressure of 200 psig and 150° C. for an additional three hours
- customAt the end of this additional three hour period
- filtrationthe contents filtered
- distillationthe filtrate is distilled over 2 grams of calcium carbonate through a 24" Goodloe column
- customyielding the following fractions
Sources & evidence
- ORD record
- ord-d34391ea0bf845ffb38507f255ff0f8e
- Source dataset
- uspto-grants-1986_08
- Patent number
- US04604487
Linked notes
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