2444-19-1

Usage

Uses

Used in Chemical Synthesis:
4-Hydroxyphenyl Benzoate is used as a key intermediate in the synthesis of various chemical compounds. Its aromatic structure and functional groups make it a valuable building block for creating a wide range of products.
Used in Insecticide Production:
4-Hydroxyphenyl Benzoate is used as a crucial component in the production of the insecticide Pyridalyl (P997113). Its incorporation into the insecticide formulation contributes to its effectiveness in controlling pests and protecting crops.

InChI:InChI=1/C13H10O3/c14-11-6-8-12(9-7-11)16-13(15)10-4-2-1-3-5-10/h1-9,14H

Upstream product

• 98-88-4 benzoyl chloride 
• 123-31-9 hydroquinone 
• 93-99-2 benzoic acid phenyl ester 
• 2444-21-5 (4'-benzyloxyphenyl)benzoate 
• 201151-77-1 C₂₉H₃₈O₄Si 
• 14210-97-0 1,4-dibenzoyloxybenzene 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 225529-40-8 4-benzoyloxy phenyl acetate 
• 65-85-0 benzoic acid 
• 103-16-2 4-Benzyloxyphenol 
• 74206-92-1 carbonic acid benzyl ester-(4-hydroxy-phenyl ester) 
• 6411-34-3 4-allyloxyphenol 
• 37592-20-4 1,4-bis(allyloxy)benzene 

Downstream Products

• 5379-30-6 4-Benzoyloxy-2-phenylazo-phenol 
• 13985-43-8 4-hydroxy-3-nitrophenyl benzoate 
• 108955-74-4 phosphoric acid mono-(4-benzoyloxy-phenyl ester) 
• 58069-02-6 2.6-dinitro-hydroquinone-4-benzoate 
• 123-31-9 hydroquinone 
• 16090-33-8 2-nitrohydroquinone 
• 225529-40-8 4-benzoyloxy phenyl acetate 
• 88561-74-4 4-(allyloxy)phenyl benzoate 
• 109591-22-2 phosphoric acid diethyl ester-(4-benzoyloxy-phenyl ester) 
• 380153-99-1 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylbenzoate 
• 125439-41-0 4-(2-quinolinylmethoxy)phenyl benzoate 
• 132239-99-7 2-Benzoyloxy-5-hydroxy-4'-hexyl-azobenzene 
• 132240-00-7 2-Benzoyloxy-5-hydroxy-4'-hexyloxy-azobenzene 
• 78097-17-3 2-chloro-4-(benzoyloxy)phenol 

Relevant academic research and scientific papers

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.

Nickel-catalyzed deallylation of aryl allyl ethers with hydrosilanes

An efficient and mild catalytic deallylation method of aryl allyl ethers is developed, with commercially available Ni(COD)2 as catalyst precursor, simple substituted bipyridine as ligand and air-stable hydrosilanes. The process is compatible with a variety of functional groups and the desired phenol products can be obtained with excellent yields and selectivity. Besides, by detection or isolation of key intermediates, mechanism studies confirm that the deallylation undergoes η3-allylnickel intermediate pathway.

Direct hydroxylation of benzene and aromatics with H2O2 catalyzed by a self-assembled iron complex: Evidence for a metal-based mechanism

An iminopyridine Fe(ii) complex, easily prepared in situ by self-assembly of cheap and commercially available starting materials (2-picolylaldehyde, 2-picolylamine, and Fe(OTf)2 in a 2 : 2 : 1 ratio), is shown to be an effective catalyst for the direct hydroxylation of aromatic rings with H2O2 under mild conditions. This catalyst shows a marked preference for aromatic ring hydroxylation over lateral chain oxidation, both in intramolecular and intermolecular competitions, as long as the arene is not too electron poor. The selectivity pattern of the reaction closely matches that of electrophilic aromatic substitutions, with phenol yields and positions dictated by the nature of the ring substituent (electron-donating or electron-withdrawing, ortho-para or meta-orienting). The oxidation mechanism has been investigated in detail, and the sum of the accumulated pieces of evidence, ranging from KIE to the use of radical scavengers, from substituent effects on intermolecular and intramolecular selectivity to rearrangement experiments, points to the predominance of a metal-based SEAr pathway, without a significant involvement of free diffusing radical pathways.

An efficient and chemoselective deprotection of aryl tert-butyldimethylsilyl (TBDMS) ethers by NaCN

Phenolic tert-butyldimethylsilyl (TBDMS) ethers can be deprotected to yield phenols in excellent yield using sodium cyanide (NaCN) as catalyst in ethanol. The deprotectation of various phenolic TBDMS ethers were found to be very convenient, fast, high yielding and chemoselective.

Cross Redox Coupling of Aryl-Aldehydes and p-Benzoquinone

Herein, we report an unprecedented Cross Redox Coupling (CRC) reaction catalyzed by Cu(OAc)2·H2O. As a proof-of-concept, direct coupling of aromatic aldehydes (or alcohols) and p-benzoquinone led to an ester in the presence of the Cu(II)-TBHP combination. During the coupling process, the C-H bond of the aldehydes was converted directly to a C-O bond. Mechanistically, we propose that the reaction proceeded via a radical pathway. In addition, atom and electron economies were well-conserved during this CRC reaction.

Synthesis of industrially important aromatic and heterocyclic ketones using hierarchical ZSM-5 and Beta zeolites

Hierarchical ZSM-5 and Beta zeolites were investigated in the synthesis of wide range of industrially important aromatic/heterocyclic ketones by Friedel-Crafts acylation and benzoylation reactions. For comparative study, conventional ZSM-5 and Beta, and amorphous mesoporous Al-MCM-41 were investigated. Hierarchical zeolites were prepared by multi-ammonium structure directing agents whereas conventional zeolites were prepared by mono-ammonium structure directing agents. Among the catalysts investigated in this study, hierarchical Beta exhibited the highest reactant conversion in the acylation and benzoylation reactions. In this study, the systematic assessment of the catalytic activity of acid catalysts for wide range of aromatic and heterocyclic compounds is shown under one umbrella. To the best of our knowledge, these reactions over hierarchical zeolites (ZSM-5 and Beta) are reported here for the first time. Structure activity relationship is explained based on the physico-chemical properties, molecular size, reactivity of reactants, and reaction mechanism. Catalysts can be easily recovered and reused with negligible loss in the catalytic activity.

Synthesis of tricyclic precursors of cyclitols

Stereoselective syntheses of three tricyclic cyclohexenones are described. These compounds were conceived as novel precursors of synthetic conduritols, quercitols, and inositols because they allow diastereoselective C=O reductions, C=C osmylations, and C=C epoxidations to be performed. These functionalizations created up to three uniformly configured oxygen-bearing stereocenters. One of the follow-up products was a tricycle that was amenable to successive cleavages of its 1,4-dioxane and 1,3-dioxane rings. This rendered the pentaesters of neo-quercitol, which contain five stereogenic C-O bonds, with ds = 85:15. Georg Thieme Verlag Stuttgart New York.

Cerium(IV) sulfate tetrahydrate: A catalytic and highly chemoselective deprotection of THP, MOM, and BOM ethers

Tetrahydropyranyl (THP), methoxymethyl (MOM), and benzyloxymethyl (BOM) phenyl/alkyl ethers were efficiently cleaved to the corresponding parent hydroxyl compounds in good yields using catalytic amounts of Ce(SO 4)2·4H2O by microwave-assisted or conventional heating in methanol solution. Intramolecular and competitive experiments demonstrated the chemoselective deprotection of THP ethers in the presence of triisopropylsilyl (TIPS) and tert-butyldiphenylsilyl (TBDPS) phenyl ethers.

First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae

The total synthesis of certain natural phenolglycosides of the family Salicaceae, namely: salireposide, populosides A, B, and C and not occurring in plants desoxysalireposide (2-(β-d-glucopyranosyloxy)-benzylbenzoate) and per-acetate of iso-salireposide (2-(β-d-glucopyranosyloxy)-5-benzoyloxy benzyl alcohol), starting from readily available phenols and glucose was accomplished. A simple method for the synthesis of phenolglycosides derivatives of 2-acyloxy salicyl and gentisyl alcohol was developed. The key step of these natural products' synthesis is a selective removal of acetyl groups in the presence of other acyl groups.