13305-18-5

Usage

Uses

Used in Pharmaceutical Industry:
(3-chlorophenyl)hydroxyacetic acid methyl ester is used as a chemical intermediate for the development of new medications due to its unique chemical structure and reactivity.
Used in Agrochemical Industry:
(3-chlorophenyl)hydroxyacetic acid methyl ester is used as a starting material for the production of insecticides and herbicides, contributing to the development of agricultural chemicals that protect crops from pests and enhance yield.

Upstream product

• 34966-50-2 methyl 2-(3-chlorophenyl)-2-oxoacetate 
• 97070-75-2 2-(3-chlorophenyl)-2-hydroxyacetonitrile 
• 53088-68-9 methyl 3-chlorophenylacetate 
• 587-04-2 m-Chlorobenzaldehyde 
• 67-56-1 methanol 
• 16273-37-3 3-chloromandelic acid 

Downstream Products

• 181040-20-0 methyl (RS)-(3-chlorophenyl)-[2-cyano-5-(thien-3-ylmethoxy)phenoxy]acetate 
• 1584127-66-1 (S)-(+)-methyl 2-acetoxy-2-(3-chlorophenyl)acetate 
• 153294-00-9 (R)-3-chloromandelic acid methyl ester 

Relevant academic research and scientific papers

Direct Aerobic α-Hydroxylation of Arylacetates for the Synthesis of Mandelates

Aerobic α-hydroxylation of α-methylene esters has proven challenging due to overoxidation and hydrolysis of the materials. In this article, KOtBu-promoted TBAB-catalyzed α-hydroxylation of α-methylene aryl esters using O2as the oxyge

Kinetic Resolution of Allylic Alcohol with Chiral BINOL-Based Alkoxides: A Combination of Experimental and Theoretical Studies

The development and characterization of enantioselective catalytic kinetic resolution of allylic alcohols through asymmetric isomerization with chiral BINOL derivatives-based alkoxides as bifunctional Br?nsted base catalysts were described in the study. A number of chiral BINOL derivatives-based alkoxides were synthesized, and their structure-enantioselectivity correlation study in asymmetric isomerization identified a promising chiral Br?nsted base catalyst, which afforded various chiral secondary allylic alcohols (ee up to 99%, S factor up to >200). In the mechanistic study, alkoxide species were identified as active species and the phenol group of BINOL largely affected the high reactivity and enantioselectivity via hydrogen bonding between the chiral Br?nsted base catalyst and substrates. The strategy is the first successful synthesis strategy of various chiral secondary allylic alcohols through enantioselective transition-metal-free base-catalyzed isomerization. The applicability of the strategy had been demonstrated by the synthesis of the bioactive natural product (+)-veraguensin.

New 4-aryl-1,3,2-oxathiazolylium-5-olates: Chemical synthesis and photochemical stability of a novel series of S-nitrosothiols

S-nitrosothiols (RSNOs) remain one of the most popular classes of NO-donating compounds due to their ability to release nitric oxide (NO) under non-enzymatic means whilst producing an inert disulphide by-product. However, alligning these compounds to the different biological fields of NO research has proved to be problematic due to the inherent instability of such compounds under a variety of conditions including heat, light and the presence of copper ions. 1,3,2-Oxathiazolylium-5-olates (OZOs) represent an interesting subclass of S-nitrosothiols that lock the –SNO moiety into a five membered heterocyclic ring in an attempt to improve the compound's overall stability. The synthesis of a novel series of halogen-containing OZOs was comprehensively studied resulting in a seven-step route and overall yields ranging between 21 and 37%. The photochemical stability of these compounds was assessed to determine if S-nitrosothiols locked within these mesoionic ring systems can offer greater stability and thereby release NO in a more controllable fashion than their non-cyclic counterparts.

Kinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Mild rhodium(III)-catalyzed C-H allylation with 4-vinyl-1,3-dioxolan-2-ones: Direct and stereoselective synthesis of (E)-allylic alcohols

A rhodium(III)-catalyzed C-H direct allylation reaction with 4-vinyl-1,3-dioxolan-2-ones has been developed. The reaction provides a facile and stereoselective access to substituted-(E)-allylic alcohols under mild and redox-neutral reaction conditions. Olefinic C-H activation is applicable, giving multifunctionalized skipped dienes in good yields. Minimal double-bond migration was observed.

1,3-Bis(2,4,6-trimethylphenyl)imidazolium chloride in combination with triethylamine: An improved catalytic system for hydroacylation/reduction of activated ketones

A rapid, economic, and high yielding methodology has been developed for hydroacylation/reduction of activated ketones by using 1,3-bis(2,4,6- trimethylphenyl)imidazolium chloride as a catalyst in combination with triethylamine. The reaction proceeded at an ambient temperature via generating N-heterocyclic carbene in situ that interacted with the (hetero)aryl aldehyde employed. While the reduction of ketones takes place in MeOH, the hydroacylation process was found to be effective in THF for both electron rich and deficient aldehydes.

Acetalsulfonate derivative, process for producing the same, and process for producing styrene oxide derivative

There are provided an acetalsulfonate derivative useful as an intermediate for medicines and agricultural chemicals, a process for industrially producing the derivative, and a process for industrially producing a styrene oxide derivative from the acetalsulfonate derivative or from a mandelic acid derivative. A process for producing an acetalsulfonate derivative which comprises a first step of esterifying a mandelic acid derivative to form a mandelic ester derivative, a second step of protecting the mandelic ester derivative by an acetal to form an acetal derivative, a third step of reducing the acetal derivative to form an ethanediol derivative and a fourth step of reacting the ethanediol derivative with a sulfonyl chloride derivative. A process for producing a styrene oxide derivative which comprises a deprotecting step of deacetalizing the acetalsulfonate derivative and a step of epoxidizing the sulfonate derivative obtained in the deprotecting step with the aid of a base catalyst.

Selective ET(A) antagonists. 5. Discovery and structure-activity relationships of phenoxyphenylacetic acid derivatives

The fifth paper in this series describes the culmination of our investigations into the development of a potent and selective ETA receptor antagonist for the treatment of diseases mediated by ET-1. Receptor site mapping of several ETA antagonists prepared previously identified a common cationic binding site which prompted synthesis of phenoxyphenylacetic acid derivative 13a, which showed good in vitro activity (IC50 59 nM, rat aortic ET(A)). Optimization of 13a led to the identification of 27b, which exhibited an IC50 of 4 nM. Although this did not translate into the expected in vivo potency, a compound of comparable in vitro activity, 27a (RPR118031A), showed a far better pharmacokinetic profile and in vivo potency (75 μmol/kg) and was duly proposed and accepted as a development candidate.

THIAZOLE AND OXAZOLE-BASED BETA3 ADRENERGIC RECEPTOR AGONISTS

Compounds having the formula STR1 and pharmaceutically acceptable salts thereof where A is STR2 R 3 is--(CH 2) n--or in the case where R 2 is STR3 R 3 in addition to the above may be STR4 R 4 is hydroxy, alkoxy, amino, alkylamino or dialkylamino; R 5 is hydrogen, fluorine, chlorine, bromine, iodine,--CN, CF 3, lower alkyl, lower alkoxy, cycloalkyl or aryl;R 6 is lower alkyl, cycloalkyl or aryl;R 7, R 7 ', R 8 and R. sub.8 ' are independently hydrogen or a lower alkyl or R. sub.7 and R 8 may together be CH 2 CH 2 ; Z is hydrogen or STR5 m is an integer of 1 or 2; n is zero or an integer of 1 to 6; andp is an integer of 1 to 5. These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.