2,2,4,4-Tetramethyl-1,3-cyclobutanedione → 2,2,4,4-Tetramethylcyclobutane-1,3-diol

HRID 591093

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].C(O)(C)C>[CH3:7][C:4]1([CH3:8])[CH:5]([OH:6])[C:2]([CH3:10])([CH3:1])[CH:3]1[OH:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A 2 liter Parr autoclave was charged with 100 grams of 2,2,4,4-tetramethylcyclobutane-1,3-dione, 300 grams of isopropyl alcohol, and 50 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 and held for 6 hours at 3.5 MPa (500 psig). Analysis of the product by gas chromatography indicated that 99.8% conversion of the 2,2,4,4-tetramethylcyclobutane-1,3-dione was obtained with 99.9% selectivity to 2,2,4,4-tetramethycyclobutane-1,3-diol with a cis:trans ratio of 1.54:1.

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-377271b9f9174f0c93163bcf87f305b7
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238602B1

Linked notes

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