4-Hydroxy-2-phenethyl alcohol

Tetrafluoroboric acid-diethyl ether complex (catalytic amount) was added to a stirred solution of epoxide (+/-)-(3aa,6a,7a,7aa)-6,7-epoxy-3a,6,7,7a-tetrahydrobenzo[d]-l,3-dioxol-2-one (32 mg, 0.2 mmol) and (R)-(+)-sec-phenethyl alcohol (0.048 ml, 0.4 mmol) in DCM at RT under argon. After 30 min, water was added and the mixture extracted with DCM (3 times). The combined organic phase was dried (MgS04) and evaporated in vacuum. Column chromatography (30-75% ether-petrol, gradient elution) of the residue afforded the alcohols [3aR-[3aa,4a,5p(R),7aa]-3a,4,5,7a-tetrahydro-4-hydroxy-5-(l-phenylethoxy)benzo[d]-l,3-dioxol-2-one and [3aS-[3aa,4a,5P(R),7aa]-3a,4,5,7a-tetrahydro-4-hydroxy-5-(l-phenylethoxy)benzo[d]-l,3-dioxol-2-one. (37 mg, 67%) as a thick oil and a 1 1 mixture of diastereomers. Subsequent HIPLC (l -Dynamax 83,123-6 column 6% isopropanol-petrol, 15 ml/min) effected separation of the diastereomers. Less polar [3aR-[3aa,4a,5p(R),7aa]-3a,4,5,7a-tetrahydro-4-hydroxy-5-(l-phenylethoxy)benzo[d]-l,3-dioxol-2-one had retention time 16.3 min [a]D2° +90.1° (c 1.1, CHCI3). 

Hydroxyphenamate. 2-Phenyl-l,2-butanediol 1-carbamate carbamic acid ft -ethyl -0-hydroxy phenethy] ester d-ethyl-p-hydroxyphenethy] carbamic acid ester 0-ethyl-0-hydroxy phenethyl carbemate 2-hydroxy-2-phenyl-butyl carbamate Al 0361 Listica. C.,H.sNOv mol wt 209.24. C 63.14%, H 7.23%, N 6.69%, O 22 94%. Prepd from d-ethyl -d-hydroxyphenethyl alcohol and ethyl chloro-formate followed by reaction with ammonia Sifferd, Brait-berg. U,S. pat. 3,066,164 (1962 to Armour-Pharm.). Pharmacology and toxicology Bastian, Clements, Di-V. Nerv. Sys. 22, 9 (1961). 

Mandelic acid derivatives are useful resolving agents. While (/ )-( +)-phenethyl alcohol (77) is commercially available, it is relatively expensive. As shown in Scheme 16, (5)-l can be converted readily into multigram quantities of 77. Reduction of 1 with borane-dimethyl sulfide provides the diol 76, which is selectively tosylated at the primary hydroxy position and then detosylated with lithium aluminum hydride to provide 77 in 48% overall isolated yield (Scheme 16). The low yield is a result of the problematic tosylation step, in which ditosylation is unavoidable. 

Aminoacridine hydrochloride 2-Amino-5-nitrothiazole Chloramine-B Chloramine-T Coffee (Coffea arabica) extract Gentamycin sulfate Hexamethylenetetramine 4-Hydroxy-3-nitrophenyl arsonic acid Phenethyl alcohol Sulfamethizole... 

A solution of 192 g of 1 -phenethyl-4-hydroxy-4-aminomethyl piperidine in BOO cc of diethyi-carbonate is heated for 1 /i hours to refiux at about B0°C in the presence of sodium methylate (prepared for immediate use from 2 g of sodium). After this time, the ethyl alcohol formed during the reaction is slowly distilled while the maximum temperature is reached. The excess ethyl carbonate is distilled under reduced pressure. A crystallized residue Is then obtained, which is stirred with 400 cc of water and 400 cc of ether. The solution is filtered and 125 g (77.6%) of practically pure product melting at 232°C to 233°C, are obtained. 

Hydrocinnamyl alcohol 1-Hydroxy-3-phenylpropane (3-Hydroxypropyl) benzene Phenethyl carbinol Phenylethyl carbinol Phenyl-1-propanol 3-Phenylpropanol 3-Phenyl-1-propanol 3-Phenylpropan-1-ol 3-Phenyl-n-propanol... 

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