61949-23-3

Usage

InChI:InChI=1/C11H20O2/c1-8(2)10-5-4-9(3)6-11(10)13-7-12/h7-11H,4-6H2,1-3H3/t9-,10+,11-/m1/s1

Upstream product

• 64-18-6 formic acid 
• 2216-51-5 (-)-menthol 
• 108-24-7 acetic anhydride 
• 68-12-2 N,N-dimethyl-formamide 
• 72773-04-7 N-formylbenzotriazole 
• 109-94-4 formic acid ethyl ester 
• 107-31-3 Methyl formate 
• 76358-81-1 tert-butyl(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)dimethylsilane 
• 89-78-1 menthol 
• 134965-38-1 Hex-1-en-2-yl formate 
• 72020-06-5 2-(2-isopropyl-5-methylcyclohexyloxy)tetrahydro-2H-pyran 
• 62338-23-2 (2-isopropyl-5-methylcyclohexyloxy)trimethylsilane 
• 100011-09-4 (2-Isopropyl-5-methyl-cyclohexyloxymethylene)-dimethyl-ammonium; chloride 
• 3724-43-4 Vilsmeier reagent 

Downstream Products

• 89-78-1 menthol 
• 17687-72-8 9-octylheptadecan-9-ol 

Relevant academic research and scientific papers

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.

Formyloxyacetoxyphenylmethane and 1,1-diacylals as versatile O-formylating and O-acylating reagents for alcohols

Formyloxyacetoxyphenylmethane, symmetric 1,1-diacylals and mixed 1-pivaloxy-1-acyloxy-1-phenylmethanes have been used as moisture stable O-formylating and O-acylating reagents for primary and secondary alcohols, allylic alcohols and phenols under solvent/catalyst free conditions to afford their corresponding esters in good yield.

N-Heterocyclic Carbene Catalyzed Transformylation

The N-heterocyclic carbene (NHC) catalyzed transformylation has been developed for the conversion of 1°, 2°, and 3° alcohols to the corresponding formates. The reaction employs low catalyst loadings and methyl formate as the formyl transfer reagent. The scope of the reaction is broad with 23 examples reported with good yields (59-96%). The reaction is insensitive to common nitrogen and oxygen protecting groups and can be achieved in the presence of a number of heterocycles.

Acidic ionic liquid immobilized on nanoporous Na+-montmorillonite as an efficient and reusable catalyst for the formylation of amines and alcohols

In this work, nanoporous sodium montmorillonite clay (Na+-MMT) was used as a support for the immobilization of 1-methyl-3-(trimethoxysilylpropyl)-imidazolium hydrogen sulfate. The Na+-MMT chemical modification ([Na+-MMT-[pmim]HSO4) was confirmed by a variety of techniques including Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy and potentiometric titration. The catalytic performance of this immobilized acidic ionic liquid was probed for the N-formylation of a variety of amines using formic acid under solvent-free conditions. This reagent is also useful for the formylation of benzylic alcohols. The procedure gave the products in excellent yields in very short reaction times. Also, this catalyst can be reused ten times without loss of its catalytic activity.

Formylation of amines and alcohols using aminopropylated mesoporous SBA-15 silica (APMS) as an efficient and recyclable catalyst

Aminopropylated mesoporous SBA-15 silica (APMS) is introduced as a new, recyclable and efficient catalyst for the formylation of a variety of amines and alcohols by using readily available formic acid under solvent-free conditions.

Dual behavior of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions

The dual behavior phenomenon of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions (SFRCs) is described; the governing factor is the stability of the carbonium ion generated from the alcohol; high concentration reaction conditions (HCRCs) or dilute solutions are much less suitable. In the case of benzylic alcohols, loss of optical activity was noted, whereas alkyl alcohols furnished a product with retention of stereochemistry.

Silica sulfuric acid and AI(HSO4)3: As efficient catalysts for the formylation of alcohols by using ethyl formate under heterogeneous conditions

A mixture of ethyl formate and a catalytic amount of silica sulfuric acid or Al(HSO4)3 as suitable formylating systems can formylate various alcohols to their corresponding formate ester derivatives under mild, nearly neutral and heterogeneous conditions at room temperature with good to excellent yields.

Silica triflate as an efficient reagent for the chemoselective formylation of alcohols

Silica triflate, as a new and stable silica-based reagent, is prepared by a reaction of silica gel with trifluoromethane sulfonyl chloride at room temperature. This reagent can be used for the efficient and selective formylation of alcohols in the presence of phenols in a relatively short reaction time and high yields under heterogeneous reaction conditions.

Efficient acetylation and formylation of alcohols in the presence of Zr(HSO4)4

Acetylation and formylation of alcohols with acetic and formic acids have been carried out in the presence of catalytic amounts of Zr(HSO 4)4 under mild and heterogeneous conditions.