P-Tolyl methyl ketone

Toluene reacted with III and aluminum chloride much as did benzene, except that yields were lower and tar formation more extensive. From the organic layer methyl p-tolyl ketone was isolated, while acetylation of the product from the aqueous layer led to 1,1-di-p-tolyl- 1-desoxy-D-glucitol hydrate (VI). p-/3-D-Glucopyranosyltoluene, structurally... 

SYNS p-ACETYLTOLUENE ETHANONE, l-(4-METHYLPHENYL)-(9CI) FEMA No. 2677 MELILOTAL p-METHYL ACETOPHENONE 1-METHYD4-ACETYLBENZENE METHYL-p-TOLYL KETONE... 

The same reaction with methyl p-tolyl ketone gave a ) -hydroxycyclopropyl selenide which upon treatment with p-toluenesulphonic acid underwent ring expansion to 2-methyl-2-p-tolylcyclobutanone, a precursor of a-cuparenone. ... 

Methyl o-tolyl ether. See o-Methylanisole Methyl-p-tolyl ether. See p-Methylanisole Methyl p-tolyl ketone. See4 -Methyl acetophenone... 

No stereoselectivity was observed in the formation of a 1 1 diastereomeric mixture of 2-hydroxy-2-phenylethyl p-tolyl sulfoxide 145 from treatment of (R)-methyl p-tolyl sulfoxide 144 with lithium diethylamide . However, a considerable stereoselectivity was observed in the reaction of this carbanion with unsymmetrical, especially aromatic, ketones The carbanion derived from (R)-144 was found to add to N-benzylideneaniline stereoselectivity, affording only one diastereomer, i.e. (Rs,SJ-( + )-iV-phenyl-2-amino-2-phenyl p-tolyl sulfoxide, which upon treatment with Raney Ni afforded the corresponding optically pure amine . The reaction of the lithio-derivative of (-t-)-(S)-p-tolyl p-tolylthiomethyl sulfoxide 146 with benzaldehyde gave a mixture of 3 out of 4 possible isomers, i.e. (IS, 2S, 3R)-, (IS, 2R, 3R)- and (IS, 2S, 3S)-147 in a ratio of 55 30 15. Methylation of the diastereomeric mixture, reduction of the sulfinyl group and further hydrolysis gave (—)-(R)-2-methoxy-2-phenylacetaldehyde 148 in 70% e.e. This addition is considered to proceed through a six-membered cyclic transition state, formed by chelation with lithium, as shown below . ... 

SYNS p-BENZOPHENONE, METHYL- PHENYL p-TOLYL KETONE USAF DO-54... 

Difluoroalkyl sulfinylmethyl ketones have been prepared in enantiomerically pure form from (+)-(f )-methyl p-tolyl sulfoxide in high yield (eq 12). The ketone function was then reduced with complete diastereoselectivity. 

Sulfinyl dienes were made from a,p-unsaturated esters and methyl p-tolyl sulfoxide followed by enolization of the ketone group (eq 16). ... 

Although the carbanion of (i )-methyl p-tolyl sulfoxide reacted with aldehydes and ketones with a poor diastereoselectivity, it reacts with imines with a much higher stereoselectivity as long as the imine substituent is an aromatic ring. (7 )-(-i-)-Tetrahydropalmatine was synthesized by addition of (7 )-methyl p-tolyl sulfoxide carbanion to 3,4-dihydro-6,7-dimethoxyisoquinoline (eq 17). ... 

In 1972, Tsuchihashi disclosed that the carbanion (28 Ar = p-tolyl), generated from (/ )-methyl p-tolyl sulfoxide with lithium diethylamide, adds to benzaldehyde or a-tetialone to give an adduct (29) in a dia-stereomeric ratio of 50 50 or 64 36, respectively. Additions of this carbanion to various unsymmetrical ketones are also reported to be poorly diastereoselective (for example, EtCOMe 50 50, Bu COMe 55 45, Bu COPh 70 30). Note that in the case of Ar = 2-pyridyl a chiral sulfinyl group increases the asymmetric induction observed in the addition of the corresponding carbanion to carbonyl compounds (PhCHO 80 20, R-C9H19CHO 70 30). Since diastereomer pairs of (29) are separable, chromatographic separation followed by reductive desulfurization with Raney Ni provides a method for obtaining optically active alcohols (30 Scheme 9). 

Optically active 3-keto sulfoxides are readily available from esters and methyl p-tolyl sulfoxide. The ketone function can be reduced with metal hydrides (DIBAL and ZnCl2/DIBAL) giving, with very high diastereoselectivity, opposite configurations in the resulting 3-hydroxy sulfoxides (Scheme 58). ... 

The required ketosulfoxide 69 (Scheme 15) was obtained in two steps in a one-pot procedure from 1,4-dimethoxybenzene (66). Ortho Hthiation of 66, lithium-copper exchange, and addition to methyl acrylate gave ester 67. Reaction of the anion obtained from (R)-methyl(p-tolyl)sulfoxide (68) [89] by treatment with LDA, with ester 67 afforded ketone 69. Diastereoselective addition of diethylaluminum cyanide to the carbonyl group of 69 [90] furnished sulfinylcyanohydrin 70 as the sole product. The (S) configuration of the new stereogenic center was inferred from the previous studies of acycUc P-ketosulfoxides [91,92]. 

CAS 134-84-9 EINECS/ELINCS 205-159-1 Synonyms p-Benzophenone, methyl- 4-Methyl-p-benzophenone Phenyl p-tolyl ketone Empirical C H,20 Fmnula CHAMfCOCeHs... 

CAS 134-84-9 EINECS/ELINCS 205-159-1 Synonyms p-Benzophenone, methyl- 4-Methyl-p-benzophenone Phenyl p-tolyl ketone Empirical C14H12O Formula CH3C6H4COC6H5 Properties Colorless to off-wh. cryst. powd. faint odor sol. in alcohols, benzene, ether, chloroform, common org. solvs. insol. in water m.w. 196.26 ... 

Methyl p-methylst3rryl Ketone (p-Methyl-benzylideneacetom, -p-tolyl- -bvtenone-Z, p-me(hyl- -aeetostgrene). 

See under W.Methyl.p.phenetidine. p-Methylphenacyl Alccfliol tolyl ketone, p4oluylcarbinol)... 

Acetozy.3-methyl-propiophenon 8 II120. [a-Aoetosy-athyl]-p-tolyl-keton 8, 121. Aoetozymethyl- [4-4thyl-phenyl]-keton... 

Acetophenone, methyl-/7-tolyl ketone p-chloroacetophenone, /7-bromoaceto-phenone, methyl -anisyl ketone, 2,4-di-methoxyacetophenone,2-methyl-4-metho-xyacetophenone, 5-methyl-2-methoxyace-tophenone, acetocumene, 2,5-trimethyl-acetophenone, 0-, m-, p-hydroxyaceto-phenone, 2,4-dihydroxyacetophenone, 3-methoxy-4-hydroxyacetophenone, o-nitroacetophenone, m-nitroacetopheno-ne, /7-nitroacetophenone, o-, m-, /7-ami-noacetophenone, 2-aceto-l -naphthoxy-acetic acid, 2-aceto-4-bromo-l-naphtho-xyacetic acid... 

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