Phenyl n-propyl ketone

Problem 15.14 Synthesize (a) p-methoxybenzaldehyde from benzene (b) cyclohexylethanal by hydrobora-tion and oxidation (c) phenylacetaldehyde, using 1,3-dithiane (d) phenyl n-propyl ketone from a dithiane (e) cyclohexyl phenyl ketone from PhCOOH and RLi (/) 2-heptanone, using a cuprate ... 

Cheng, C. and Tsai, H.R.J. (2008) Yeast-mediated enantioselective synthesis of chiral R-(+)- and S-(—)-l-phenyl-l-butanol from prochiral phenyl N-propyl ketone in hexane-water biphasic culture. J. Chem. Technol Biotechnol, 83, 1479-1485. 

Methyl n-Propyl Ketone n-Octone o Cyclohexanone loi Isopropyl Alcohol o Diefhylomine loi Isobutyl Acetate 2-Nitropropane 0 Triethylomine o Phenyl Acetate o Methyl Benzoate o Benzene 0 Acetone... 

This two-step sequence can synthesize many alkylbenzenes that are impossible to make by direct alkylation. For example, we saw earlier that n-propylbenzene cannot be made by Friedel-Crafts alkylation. Benzene reacts with n-propyl chloride and AICI3 to give isopropylbenzene, together with some diisopropylbenzene. In the acylation, however, benzene reacts with propanoyl chloride and A1C13 to give ethyl phenyl ketone (propiophenone), which is easily reduced to n-propylbenzene. 

DIMETHYLAMINO)PHENYL)AZO)PHENYL)-N-METHYL CETAMIDE see DPQ200 4-(DLMETHYLAMINO)PHENYL-3-(4-(4-CHLOROPHENYL)-4-HYDROXYPIPERIDINO)-PROPYL KETONE see CIC 580... 

Ketones of the type RCOCHRj, where R represents methyl, ethyl, isopropyl, -butyl, 7 -hexyl, or phenyl, and R represents ethyl, n-propyl, -butyl, or phenyl, have been prepared by a series of reactions similar to that used in the preparation of aldehydes (method 167). ... 

Phenyl propyl ketone (butyrophenone) TM 4.3b is available by common Friedel-Crafts acylation. On the other hand, ferfbutyl propyl ketone TM 4.4a is not an easily available Cg building block. Butanoic acid is produced by either fermentation of starch using the Bacillus subtilis strain or oxidation of n-butanal, available by formylation of propene (Scheme 4.3). 

A direct relationship between stereoselectivity and the distance of the stcrcogcnic center from the metal atom is observed in the reduction of 2-propyl phenyl ketone with optically active dialkylzinc compounds Zn[(CH,)n C H(CH3)Et]2 the asymmetric induction ranges from 15.2 (n = 1) to 9.3 (n = 2) to 2.4 (n = 3)% ee106. These results, nevertheless, prove that, in contrast to an earlier proposal107, the hydride must not necessarily be transferred from an asymmetric carbon atom (compare also with earlier results108). 

The same substituent effect is present with trifluoromethyl aryl ketones. N/J, AfW-Tetramethyl-N"-(f-butyl)guanidine was an effective catalyst for reaction with trifluoromethyl ketones [123]. The reaction can be done enantioselectively using 3,3 -bw-(2,4,6,-tri-j-propyl-phenyl)BlNOL [ 124],... 

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