2- Phenyl-1,3-propanediol

Chiral 4,5-dihydrooxazoles 1 are readily prepared2 by condensing (+)-(1S,2.S)-2-amino-1 -phenyl-1,3-propanediol with imino ethers at 0 °C. The isomeric side product 2 is removed upon crystallization. 

Hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl[2S,3S.8aR]-5-oxo-5H-oxazolo[3.2-a]pyridine 5H-Oxazolo[3,2-a]pyridin-5-one, hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl-, [2S-(2a,3p,8ap)]- (12) (116950-01-7) (1S,2S)-(+)-2-Amino-1-phenyl-1,3-propanediol 1,3-Propanediol, 2-amino-1 -phenyl (9) (3306-06-7)... 

Amino-1-phenyl-1,3-propanediol, (1S,2S)-(+)- 1,3-Propanediol. 2-amino-1 -phenyl ... 

Formylamino-3,5-dinitrothiophene, 1817 2-Formylamino-1 -phenyl-1,3 -propanediol, 3316 Formylhydrazine, 0472... 

Oxidation. This mild oxidizing reagent can be used for selective oxidation of benzylic and allylic alcohols. Complete conversnm requires 3 equiv. of oxidant. Primary and secondary alcohols are oxidized slowly in refluxing chloroform, but require a large excess of oxidant. An example is the selective oxidation of 1-phenyl-1,3-propanediol to 3-hydroxy-1-phenyl-1-propanone (52% yield). 

C9H13N02 (1 R,2R)-2-amino-1 -phenyl-1,3-propanediol 46032-98-8 539.82 47.723 2 17468 C9H1402 5-nonynoic acid 56630-34-3 486.73 TiiiTT 2... 

When phenylcyclopropane was treated with thallium(III) nitrate rather than thallium(III) acetate, 1-phenyl-1,3-propanediol dinitrate (5, = Ph = R = H) was obtained in ex-... 

S, S)-2-Amino-1-phenyl-1,3-propanediol (8) is commercially available and is a byproduct of the technical synthesis of the antibiotic chloramphenicol. It is comparatively inexpensive, so there is no need for laboratory synthesis. It is readily converted to dihydrooxazoles which are themselves useful auxiliaries. The synthesis of (72)-phenylalaninol from this aminodiol via a dihydrooxa-zole has been cited (Section 2.3.1.). Hydrolysis of the intermediate dihydrooxazole leads to an amino alcohol 9 methylated at oxygen which is used as a more convenient starting material for the preparation of dihydroxazoles used in enolatc reactions (Sections D. 1.3.1.4., B.2.). 

Nonen-2-ynoic acid, N-70072 1 -Phenyl-1,2-propanediol, P-80121 1 -Phenyl-1,3-propanediol, P-80122... 

Allylbenzene added to ethereal butyllithium, allowed to stand overnight at room temp., added dropwise to an ice-cooled 2 M soln. of borane in tetrahydrofuran, stirred 5 hrs., treated in turn with water, 3 N NaOH, and HgOg, the resulting crude l-phenyl-l,3-propanediol allowed to react overnight with 1 1 acetic anhydride-pyridine 1-phenyl-1,3-propanediol diacetate. Y 65%. F. e. s. J. Klein and A. 

R = H R2=CH3i 1-Phenyl-ethanol R = H R2=CH2CH3 1-Phenyl-propanol R = H R2=CH20H 1-Phenyl-1,2-elhanediol R = H p2= CH2CH2OH 1-Phenyl-1,3-propanediol R = CH3 R2 = CH2CH3 2-Phenyl-2-butanol R = CH3 p2= CH2OH 2-Phenyl-1,2-propanediol R = CH3 p2= C = CH 2-Phenyl-2-butyn-2-ol... 

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