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

HRID 591099Notes

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

Conditions

Temperature: 100 °C

Procedure

A 2 liter Parr autoclave was charged with 100 grams of 2,2,4,4-tetramethylcyclobutane-1,3-dione, 375 grams Isopar™ G, 25 grams dionized water, and 50 grams of 2% ruthenium on alumina (surface area=10 m2/g, purchased from BASF Catalysts) placed under a screen in the bottom of the autoclave. 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 1200 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-tetramethylcyclobutane-1,3-dione was obtained with 100% selectivity to 2,2,4,4-tetramethycyclobutane-1,3-diol with a cis:trans ratio of 19.8:1.

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-70aff4ed7f4a427581f526c312dff077
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238602B1

Reaction notes

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