3102-00-9

Usage

Originator

Valbil,Rohm Pharma,W. Germany,1981

Manufacturing Process

Initially, 4.5 g (0.08 mol) pulverized potassium hydroxide was dissolved in 300 ml isopropanol in a 500 ml four-neck flask equipped with stirrer, intensive cooler, dropping funnel and feed pipe for the gas treatment with nitrogen.Then, 52.0 g (0.4 mol) n-butylglycidyl ether and 41.4 g (0.44 mol) phenol was added thereto, whereafter the material was heated to boiling under nitrogen. The material was stirred, about 8.5 hours, until no glycidyl ether could be determined, e.g., by gas chromatography.After the suspension was cooled under nitrogen, the solvent was distilled off under vacuum. The residue was taken up in 200 ml water and the milky emulsion extracted exhaustively with ether. From the organic phase, the excess butylglycidyl ether was extracted with diluted potassium hydroxide solution. The ether phase was washed neutral with water and the solvent removed after drying with sodium sulfate. The remaining oily residue was distilled under vacuum; there was obtained a colorless liquid of BP 123.5°C/0.07 mm. Yield: 81.8 g (91.1% of the theory)

Therapeutic Function

Choleretic

InChI:InChI=1/C13H20O3/c1-2-3-9-15-10-12(14)11-16-13-7-5-4-6-8-13/h4-8,12,14H,2-3,9-11H2,1H3

Upstream product

• 122-60-1 Phenyl glycidyl ether 
• 71-36-3 butan-1-ol 
• 5593-70-4 titanium (IV) butoxide 

Relevant academic research and scientific papers

Asymmetric Transfer Hydrogenation of 1,3-Alkoxy/Aryloxy Propanones Using Tethered Arene/Ru(II)/TsDPEN Complexes

A series of propanones containing combinations of aryloxy and alkoxy substituents at the 1- and 3-positions were reduced to the alcohols via asymmetric transfer hydrogenation using a tethered Ru(II)/TsDPEN catalyst. The enantioselectivities of the reductions reveal a complex pattern of electronic and steric effects which, when used in a matched combination, can lead to the formation of products of up to 68% ee (84:16 er) from this highly challenging class of substrate.

Efficient and regioselective ring-opening of epoxides with alcohols and sodium azide by using catalytic amounts of gacl3/polyvinylpyrrolidone

A new polymeric catalyst was prepared by supporting GaCl3 on cross-linked polyvinylpyrrolidone (GaCl3/ PVP). This catalyst was employed for efficient and regioselective ring-opening reaction of epoxides by various alcohols under solvent-free conditions at room temperature. In our procedure, this heterogeneous catalyst was used at neutral and mild reaction conditions to afford high yields of β-alkoxy alcohols. Also, regioselective conversion of epoxides to β-azidohydrines was accomplished by sodium azide in MeOH in the presence of GaCl3/PVP at room temperature. GaCl3/PVP is a non-hygroscopic and recoverable catalyst and is easily separated from reaction mixture by a simple filtration and re-used repeatedly. Also, this catalyst has good handling and can be stored for long time without any reducing of its reactivity.

Reaction of 2,3-epoxypropyl ethers with 1-butanol

Nucleophilic opening of the oxirane ring in 2,3-epoxypropyl ethers with alcohols in the presence of titanium alkoxides and other catalysts was studied. The mechanism of catalysis by titanium alkoxides was discussed on the basis of comparison with acid-bas

Silica sulfuric acid; an efficient and reusable catalyst for regioselective ring opening of epoxides by alcohols and water

The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of silica sulfuric acid with high degree of regioselectivity. The catalyst is reusable and can be applied several times without any decrease in the yield of reactions.

ALKOXYLATION OF SUBSTITUTED OXIRANES BY ALKOXYTITANIUN TOSYLATES

Under mild conditions alkoxytitanium tosylates convert substituted oxiranes into the monoethers of 1,2-glycols with high regioselectivity.