27602-75-1

Basic information

• Product Name: 6-methoxy-alpha-methylnaphthalen-1-acetaldehyde
• Synonyms: 6-methoxy-alpha-methylnaphthalen-1-acetaldehyde;2-(Methoxynaphthalene-2-Yl);2-Methoxy Naphthalene-2-yl) Propionaldehyde;6-Methoxy-α-methyl-2-naphthaleneacetaldehyde
• CAS NO: 27602-75-1
• Molecular Formula: C₁₄H₁₄O₂
• Molecular Weight: 214.25976
• EINECS: 248-558-6
• Mol File: 27602-75-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 42 °C
• Boiling Point: 356.8 °C at 760 mmHg
• Flash Point: 161.9 °C
• Appearance: /
• Density: 1.099 g/cm³
• CAS DataBase Reference: 6-methoxy-alpha-methylnaphthalen-1-acetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methoxy-alpha-methylnaphthalen-1-acetaldehyde(27602-75-1)
• EPA Substance Registry System: 6-methoxy-alpha-methylnaphthalen-1-acetaldehyde(27602-75-1)

Safety Data

• Hazardous Substances Data: 27602-75-1(Hazardous Substances Data)

Usage

Uses

Naproxenal, is an impurity of Naproxen (N377525), an anti-inflammatory, analgesic, antipyretic. A non-steroidal anti-inflammatory.

Upstream product

• 58902-04-8 (E)-2-methoxy-6-(prop-1-en-1-yl)naphthalene 
• 23981-80-8 naproxen 
• 63444-51-9 2-methoxy-6-vinylnapthalene 
• 108781-65-3 1-(6-methoxy-2-naphthyl)ethanol 
• 32305-59-2 S-2-(6-methoxy-2-naphthyl)propionaldehyde 
• 31220-35-6 (R,S) naproxen ethyl ester 
• 201230-82-2 carbon monoxide 
• 138623-03-7 tert-butyl α-(6-methoxynaphthalen-2-yl)propionate 
• 90708-65-9 1-(6-methoxy-2-naphthyl)-prop-1-ene 
• 27602-74-0 2-(6-methoxynaphth-2-yl)-1,2-propylene oxide 
• 79-37-8 oxalyl dichloride 
• 37414-52-1 2-(6-methoxy-2-naphthyl)-propyl alcohol 
• 154238-67-2 3-(2-methoxynaphthalen-6-yl)prop-2-en-1-ol 
• 3900-45-6 6-methoxy-2-acetylnaphthalene 

Downstream Products

• 27602-76-2 2-(6-methoxy-2-naphthyl)propanal oxime 
• 3900-45-6 6-methoxy-2-acetylnaphthalene 
• 26159-36-4 naproxol 

Relevant articles and documents

Copper-catalyzed hydroformylation and hydroxymethylation of styrenes

Hydroformylation catalyzed by transition metals is one of the most important homogeneously catalyzed reactions in industrial organic chemistry. Millions of tons of aldehydes and related chemicals are produced by this transformation annually. However, most of the applied procedures use rhodium catalysts. In the procedure described here, a copper-catalyzed hydroformylation of alkenes has been realized. Remarkably, by using a different copper precursor, the aldehydes obtained can be further hydrogenated to give the corresponding alcohols under the same conditions, formally named as hydroxymethylation of alkenes. Under pressure of syngas, various aldehydes and alcohols can be produced from alkenes with copper as the only catalyst, in excellent regioselectivity. Additionally, an all-carbon quaternary center containing ethers and formates can be synthesized as well with the addition of unactivated alkyl halides. A possible reaction pathway is proposed based on our results. This journal is

Synthesis of rac-ɑ-aryl propionaldehydes via branched-selective hydroformylation of terminal arylalkenes using water-soluble Rh-PNP catalyst

This work detailed the preparation of a class of water-soluble PNP ligands that differed by the nature of the substitute on phenyl ring of ligands. These ligands were incorporated into water-soluble rhodium-PNP complex catalysts that were used to regioselective hydroformylation of a series of terminal arylalkenes, providing efficient access to rac-α-aryl propionaldehydes in good to excellent yield (up to 97%) and branched-regioselectivity (up to 40:1 b/l ratio). Furthermore, gram-scale and diverse synthetic transformation demonstrated synthetic application of this methodology for non-steroidal antiinflammatory drugs.

New process for synthesizing racemic naproxen based on Heck coupling

The invention discloses a novel process for synthesizing racemic naproxen based on Heck coupling, which comprises the following steps: (1) carrying out Heck coupling reaction on 2-X substituted-6-methoxynaphthalene and crotonamide in an aprotic organic solvent under the action of a palladium catalyst and alkali to generate 3-(6-methoxynaphthyl-2-)-crotonamide; and (2) carrying out Hofmann degradation reaction on the 3-(6-methoxynaphthyl-2-)-crotonamide in an alkaline solution of hypochlorite to generate 2-(6-methoxynaphthyl-2-)-propionaldehyde, directly adding the 2-(6-methoxynaphthyl-2-)-propionaldehyde into chlorite without separation, and conducting oxidizing at room temperature to obtain racemic naproxen. The process provided by the invention does not need to prepare a highly active Grignard reagent, does not need a harsh anhydrous condition, and is relatively high in conversion rate and easy in product purification.