22201-45-2

Usage

InChI:InChI=1/C22H26O3/c1-21(2,3)17-11-7-15(8-12-17)19(23)25-20(24)16-9-13-18(14-10-16)22(4,5)6/h7-14H,1-6H3

Upstream product

• 108-24-7 acetic anhydride 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 1710-98-1 p-tert-butyl benzoyl chloride 
• 201230-82-2 carbon monoxide 
• 35779-04-5 1-tert-butyl-4-iodobenzene 
• 939-97-9 4-tert-Butylbenzaldehyde 
• 877-65-6 p-tert-butylbenzyl alcohol 
• 615-36-1 2-bromoaniline 

Downstream Products

• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 1178005-94-1 C₂₀H₁₈O₄ 
• 60561-82-2 1-(4-(tert-butyl)phenyl)-2-methylpropan-1-one 
• 1380434-50-3 1-(4-tert-butylphenyl)-3,3-dimethoxypropan-1-one 
• 1384969-46-3 4-(4-(tert-butyl)phenyl)-4-oxobutyl 4-methoxybenzoate 
• 1380434-49-0 4-(4-(tert-butyl)phenyl)-3-methyl-4-oxobutyl 4-cyanobenzoate 
• 1384969-44-1 4-(4-(tert-butyl)phenyl)-3-methyl-4-oxobutyl 2-methoxybenzoate 
• 1384969-49-6 piperidine-1,4-diylbis((4-(tert-butyl)phenyl)methanone) 
• 914220-77-2 1-(4-(tert-butyl)phenyl)pentan-1-one 
• 1384969-52-1 2-(4-(4-(tert-butyl)phenyl)-3-methyl-4-oxobutyl)isoindoline-1,3-dione 
• 1380434-51-4 1-(4-tert-butylphenyl)-2-(trimethylsilyl)ethanone 
• 1017160-42-7 (4-(tert-butyl)phenyl)(cyclopentyl)methanone 
• 28047-27-0 (4-(tert-butyl)phenyl)(cyclohexyl)methanone 
• 1380434-18-3 (4-(tert-butyl)phenyl)(1-tosylpiperidin-4-yl)methanone 

Relevant academic research and scientific papers

Metal-free oxidative self-coupling of aldehydes or alcohols to symmetric carboxylic anhydrides

A metal-free synthesis of symmetrical anhydrides has been developed starting from aldehydes, both aliphatic and aromatic or primary benzylic alcohols. The reaction occurs at room temperature and makes use of trichloroisocyanuric acid (TCCA) as an oxidant providing the desired carboxylic anhydrides in satisfactory yields.

Anhydrides from aldehydes or alcohols via oxidative cross-coupling

A novel type of metal-free oxidative cross-coupling for the synthesis of symmetrical and mixed anhydrides from aldehydes or benzylic alcohols has been developed. The aldehydes or alcohols were converted in situ into their corresponding acyl chlorides, which were then reacted with an array of carboxylic acids. The methodology has a general applicability, and was successfully employed to prepare either aromatic or aliphatic symmetrical anhydrides and mixed anhydrides, which are very unstable compounds.

Oxidative self-coupling of aldehydes in the presence of CuCl2/TBHP system: Direct access to symmetrical anhydrides

A simple synthesis of symmetrical anhydrides has been developed. Using tert-butylhydroperoxide (TBHP) as the oxidant and copper(II) chloride as the catalyst in acetonitrile, various aromatic and heteroaromatic aldehydes were reacted to provide symmetrical anhydrides in modest to good yields.

Light-enabled synthesis of anhydrides and amides

Recently, we have demonstrated that the photogeneration of Vilsmeier-Haack reagents is possible using only dimethylformamide (DMF) and tetrabromomethane (CBr4) in the bromination of alcohols. Extending these findings to carboxylic acid substrates has produced a mild and facile approach to the in situ formation of symmetric anhydrides, which were conveniently converted to amide derivatives in a one-pot process. The efficient protocols discussed herein are marked by use of UVA LEDs (365 nm), which have reduced the reaction times and come with a low setup cost.

Carboxylic acid anhydrides via Pd-catalyzed carbonylation of aryl halides at atmospheric CO pressure

A convenient method has been developed, which allows for the direct transformation of aryl iodides into the corresponding carboxylic acid anhydrides via Pd-catalyzed carbonylation under atmospheric CO pressure. The Royal Society of Chemistry 2012.

Synthesis of symmetric anhydrides using visible light-mediated photoredox catalysis

A new approach to anhydride formation is reported via activation of C-O bonds by the Vilsmeier-Haack reagent formed by Ru(bpy)3Cl2 and CBr4 in DMF. Various aryl and alkyl carboxylic acids are converted to the corresponding anhydrides in excellent yields.

Processes for preparing gonadotropin releasing hormone receptor antagonists

The present invention relates to methods of making Gonadotropin Releasing Hormone (“GnRH”) (also known as Leutinizing Hormone Releasing Hormone) receptor antagonists.

A convenient method for synthesis of symmetrical acid anhydrides from carboxylic acids with trichloroacetonitrile and triphenylphosphine

Various carboxylic acids are converted into the corresponding carboxylic acid anhydrides treated with trichloroacetonitrile and triphenylphosphine in the presence of triethylamine at room temperature.

COBALT(II) CHLORIDE CATALYZED SYNTHESES OF ACID ANHYDRIDES FROM ACID CHLORIDES

Acid anhydrides were synthesized by reacting acid chlorides with carboxylic acids in the presence of catalytic quantities of cobalt(II) chloride.