Methoxy benzoyl chloride

SYNS p-ANISYOL CHLORIDE BENZOYL CHLORIDE, METHOXY-(9CI) METHOXY-BENZOYL CHLORIDE... 

Synonyms Anisoyl chloride 4-Anisoyl chloride Benzoyl chloride, methoxy- Benzoyl chloride, 4-methoxy- 4-Methoxybenzoic acid chioride p-Methoxybenzoic acid chloride Methoxybenzoyl chloride 4-Methoxybenzoyi chloride p-Methoxybenzoyl chloride Empirical C8H7CIO2 Formula CH3OC6H4COCI Properties Clear cryst. or amber liq. sol. in acetone, benzene, ether dec. by water and alcohol fumes in moist air m.w. 170.60 m.p. 22 C b.p. 262-263 C flash pt. 87 C Toxicology Sol ns. corrosive to tissue (skin, eyes, mucous membranes) lachrymator TSCA listed... 

Benzoyl chloride, methoxy- Benzoyl chloride, 4-methoxy-. See p-Anisoyl chloride Benzoyl chloride, 3-nitro- Benzoyl chloride, m-nitro-. See m-Nitrobenzoyl chloride N-Benzoyl-N-(3-chloro-4-fluorophenyl)-DL-alanine 1-methylethyl ester. SeeFlamprop-isopropyl... 

Preparation by Friedel-Crafts acylation of chlorobenzene with 3-chloro-4-methoxy-benzoyl chloride in the presence of alnmininm chloride at 120° for 3 h (50-70%) [931]. 

SM was prepared in two steps first, formation of N-[3-[(tert-butyldimethylsilyl) oxy]-4-methoxybenzoyl]morpholine (SMI) by action of 3-[(tert-butyldimethyl-silyl)oxy]-4-methoxy-benzoyl chloride with morphohne in toluene for 4 h at r.t. under argon. Then, the amide SMI was allowed to react with the hthium derivative prepared from 3,4,5-trimethoxybromobenzene [1178] and tert-butyllithium in tetrahydrofuran at -78° to give SM [1177]. 

Preparation by reaction of 3-ethoxy-4-methoxy-benzoyl chloride with 2,5-dimethoxyphenetole in the presence of aluminium chloride in ethyl ether at r.t. for 48 h (23%) [1174]. 

Obtained by reaction of methylmagnesium bromide with 5-chloro-2-methoxy-benzoyl chloride in the presence of bis[2-(N,N-dimethylamino)ethyl] ether in... 

Obtained by decomposition of l-(2-acetoxy-5-methoxy-phenyl)-2-diazoethanone in methanol with copper bronze (57%). The diazoketone (dark reddish liquid) was prepared by reaction of diazomethane with 2-acetoxy-5-methoxy-benzoyl chloride in ethyl ether [4820]. 

Production of cellulose esters from aromatic acids has not been commercialized because of unfavorable economics. These esters are usually prepared from highly reactive regenerated cellulose, and their physical properties do not differ markedly from cellulose esters prepared from the more readily available aHphatic acids. Benzoate esters have been prepared from regenerated cellulose with benzoyl chloride in pyridine—nitrobenzene (27) or benzene (28). These benzoate esters are soluble in common organic solvents such as acetone or chloroform. Benzoate esters, as well as the nitrochloro-, and methoxy-substituted benzoates, have been prepared from cellulose with the appropriate aromatic acid and chloroacetic anhydride as the impelling agent and magnesium perchlorate as the catalyst (29). 

Pyridazine 1-oxides substituted at position 3 or positions 3 and 6 afford the corresponding 5-nitro derivatives. A methyl group at position 6 (a with respect to the iV-oxide group) is frequently converted into the cyano group, and a methoxy group at position 6 is demethy-lated by benzoyl chloride/silver nitrate. For example, 3-substituted 6-methylpyridazine 1-oxides give the 5-nitro derivatives (96) and the 6-cyano-5-nitro derivatives (97), whereas... 

Methoxypyridazine 1-oxide reacts with methyl /3-aminocrotonate in the presence of benzoyl chloride to give a-(6-methoxy-3-pyridazinyl) /3-aminocrotonate (112) which can be converted by mild hydrolysis into the corresponding acetate (113 Scheme 34) <78JHC1425). 

This method is an adaptation of that of Dengel. -Methoxy-phenylacetonitrile can also be prepared by the metathetical reaction of anisyl chloride with alkali cyanides in a variety of aqueous solvent mixtures by the nitration of phenylaceto-nitrile, followed by reduction, diazotization, hydrolysis, and methylation 1 by the reduction of ct-benzoxy- -methoxy-phenylacetonitrile (prepared from anisaldehyde, sodium cyanide, and benzoyl chloride) and by the reaction of acetic anhydride with the oxime of -methoxyphenylpyruvic acid. ... 

A solution of 5-methoxy-6//-l, 4-diazepine (0.386 g, 3.1 mmol) and benzoyl chloride (0.550 g, 3.9 mmol) in pyridine (5 mL) was kept for 2 d in a refrigerator and ice-water (15 mL) was then added. The mixture was extracted with CH2C12 and the extract was washed with H20. dried and concentrated under reduced pressure. The residue was chromatographed (alumina, benzene) to give the product yield 0.420 g (65%) oil. 

Benzene, l-(l,l-dimethylethyl)-3-methyl-2, 4-dinitro Benzoyl chloride, 6-(l, l-dimethylethyl)-3-methyl-2, 4-dinitro-Benzene, 1, 3-dibromo-2- (l,l-dimethylethyl)-5-methoxy-4-nitro Benzonitrile, 2-(l,l-dimethylethyl)-4, 5-dimethyl-3-nitro-Benzene, l-(l,l-dimethylethyl)-3-methoxy-5-methyl-2, 4, 6-trinitro... 

Reticuline (38), one of the most important intermediates in the biosynthesis of opium alkaloids, has been synthesized in racemic form (Scheme 7) (78). 6-Methoxy-7-benzyloxyisoquinoline (39), prepared from O-benzylisovanillin via a modified Pomeranz-Fritsch isoquinoline synthesis, was treated with benzoyl chloride and potassium cyanide to obtain Reissert compound 40. Alkylation of the anion generated from 40 with 3-benzyloxy-4-methoxybenzyl chloride gave the corresponding 1-substituted Reissert compound 41 which was hydrolyzed in alkaline medium to 1-benzylisoquinoline derivative 42. Quatemarization of 42 with methyl iodide followed by sodium borohydride reduction and debenzylation led to ( )-reticuline (38) in about 25% overall yield from 39. 

Two other nucleophilic substitution reactions of pyridine iV-oxides deserve mention and further study to determine the effects of substituents. Pyridine N-oxide, benzoyl chloride, and the piperidine enamine of cyclohexanone give a good yield of 2-(2 -pyridyl)cyclo-hexanone (155) (63%).360 When W-methoxy-4-picolinium methyl... 

Chiral a-methoxy aldehydes. The anion ot (S)-l reacts with benzoyl chloride to give two products (2) in the ratio 99 1. L1A1H4 reduction of 2a, 2b gives only two a-tolylthio-p-hydroxy sulfoxides (3a,b) rather than the expected four diastereomers. Evidently the LiAlHi reduction is highly regiospecific. Either 2 or 3 can be separated by crystallization or chromatography and converted into optically pure a-methoxy aldehydes (4, equation 1). 

---