2,2,4,4-Tetramethyl-1,3-cyclobutanedione → 2,2,4,4-Tetramethylcyclobutane-1,3-diol
Reaction equation
[CH3:1][C:2]1([CH3:10])[C:5](=[O:6])[C:4]([CH3:8])([CH3:7])[C:3]1=[O:9]>[Ru].O>[CH3:7][C:4]1([CH3:8])[CH:5]([OH:6])[C:2]([CH3:10])([CH3:1])[CH:3]1[OH:9]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A 300 mL Parr autoclave was charged with 25 grams of 2,2,4,4-tetramethylcyclobutane-1,3-dione, 87.50 grams Isopar™ G, 12.50 grams of water, and 12.5 grams of 2% ruthenium on alumina (surface area=10 m2/g, purchased from BASF Catalysts). The autoclave was pressure purged three times with nitrogen and three times with hydrogen, and the pressure was increased to 3.5 MPa (500 psig) with hydrogen. The autoclave was heated to 100° C. with stirring at approximately 1400 rpm and held for 4 hours at 3.5 MPa (500 psig). Analysis of the product by gas chromatography indicated that complete conversion of the 2,2,4,4-tetramethyl-1,3-cyclobutanedione was obtained with 99.9% selectivity to 2,2,4,4-tetramethycyclobutane-1,3-diol with a cis:trans ratio of 17.2:1.
Workup
- custompurged three times with nitrogen and three times with hydrogen
- temperaturethe pressure was increased to 3.5 MPa (500 psig) with hydrogen
Sources & evidence
- ORD record
- ord-a624a255981a447eb9ca482bb41fd3f6
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238602B1
Reaction notes
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