Aldrich Chemical Co., Inc

CatakgEIandbook ofPine Chemicals, 1994-1995, Aldrich Chemical Co. Inc., Milwaukee, Wis., 1994. 

J. G. Grasselli and W. M. Ritchey, CK.CA.tlas of Spectral Data and Physical Constants of Organic Compounds 2nd ed., CRC Press Inc., Boca Raton, Fla., 1975. A. A. Swigar and R. M. Silversteia, Monotepenes, Infrared, Mass, M-NMR, and C-NMR Spectra, and Korats Indices, Aldrich Chemical Co., Inc., Milwaukee, Wis., 1981. 

The neopentanedlol and triethyl orthoformate were purchased from Aldrich Chemical Co., Inc. and used as received. Failure to distil the methyl vinyl ketone, also obtained from Aldrich Chemical Co., to a clear, colorless liquid before use resulted in difficulty in determining the endpoint of the reaction with HBr. Therefore, the methyl vinyl ketone was distilled prior to use at reduced pressure. 

Butyraldehyde is supplied by Aldrich Chemical Co., Inc., and Eastman Organic Chemicals. The aldehyde was freshly distilled before use. Triethyl-amine was dried over potassium hydroxide pellets and distilled. 

Deoxy-l, 3,4,6-tetra-O-p-nitrobenzoyl-D-lyxo-hexose. To a stirred suspension of 4.64 grams (25 mmoles) of p-nitrobenzoyl chloride in 50 ml. of anhydrous pyridine at 0°C. is added, in small portions over a period of 15 minutes, 0.82 grams (5 mmoles) of 2-deoxy-D-Zt/xo-hexose purchased from Aldrich Chemical Co., Inc., Milwaukee, Wis. Stirring is maintained at 0°C. for 2 hours and the mixture is kept in a refrigerator... 

Experiments were carried out using isotopically labelled methanol (97% 0) and ethanol (98% purchased from MSD Isotopes. Anhydrous isobutanol was purchased from Aldrich Chemical Co., Inc. and contained the natural abimdances of orygen isotopes, i.e. 99.8% and 0.2% O. Nafion-H was obtained fi om C. G. Processing, Inc. and Amberlyst resins were provided by Rohm and Haas. The 2SM-5 zeolite was provided by Mobil Research Development Corp. H-Mordenite, montmorillonite K-10, and silica-alumina 980 were obtained firom Norton, Aldrich, and Davison, respectively. y-AIumina was prepared from Catapal-B fi om Vista. 

The l-bromo-3-phenylpropane was obtained from Columbia Organic Chemicals Co., Inc., Columbia, South Carolina, and from Aldrich Chemical Co., Inc., Milwaukee, Wisconsin. Redistillation of the commercial material does not noticeably affect yields. 

Bromo-2-naphthoic add (1, 98%, Sigma Chemical Co.), 3.5-dimethylphenol (2, >98%, Merck-Schuchard), 1,3-dicyclohexylcarbodiimide (DCC, 99%, Merck-Schuchard), and 4-(dimethylamino)pyridine (DMAP, 99%, Aldrich Chemical Co., Inc.) were used as received. Dichloromethane was distilled from phosphorus pentoxide and stored over activated molecular sieves (4A). 

Dichloromethane and triethylamine were distilled from calcium hydride before use. Silica gel 60. 0.040-0.063 mm (Merck) was used for column choromatography. Lithium aluminum hydride (95%, powder) was obtained from Aldrich Chemical Co., Inc. 

Fluoroanisole was purchased from Aldrich Chemical Co., Inc., and used without further purification. 

The CBS-catalyst [(S)-2-methyl-CBS-oxazaborolidine] (S)-5 (1.0 M in toluene) (The CBS catalyst is named after Corey, Bakshi, and Shibata) and the borane-THF complex (1.0 M in THF) were obtained from Aldrich Chemical Co., Inc. and used as received. THF was distilled from potassium directly before use. 

A. A. Swigar and R. M. Silverstein, Monoterpenes, Infrared, Mass, H-NMR, and UC-NMR Spectra, andKovats Indices, Aldrich Chemical Co., Inc., Milwaukee, Wis., 1981. 

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