37832-34-1

Usage

Physical state

Colorless liquid

Structure

Benzene ring with two methoxymethyl groups attached at the 1 and 4 positions

Uses

a. Fragrance ingredient
b. Production of flavor compounds
c. Organic synthesis as a protecting group for aldehydes

Stability

Relatively stable

Toxicity

Low toxicity, making it safe for various applications

InChI:InChI=1/C12H18O4/c1-13-11(14-2)9-5-7-10(8-6-9)12(15-3)16-4/h5-8,11-12H,1-4H3

Upstream product

• 67-56-1 methanol 
• 106-42-3 para-xylene 
• 623-27-8 terephthalaldehyde, 
• 1592-31-0 1,4-bis(dibromomethyl)benzene 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 103781-93-7 4-(dimethoxymethyl)benzenecarbaldehyde 
• 124-41-4 sodium methylate 
• 149-73-5 trimethyl orthoformate 
• 106456-88-6 4-(5,5-dimethyl-1,3-dioxan-2-yl)benzaldehyde 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 161772-86-7 methyl 4-(2,6,10-trimethyl-1,3,5,9-undecatetraenyl)cinnamate 
• 161772-89-0 (E)-3-[4-((E)-2-Methyl-3-oxo-propenyl)-phenyl]-acrylic acid methyl ester 
• 161772-88-9 4-((E)-2-Methyl-3-oxo-propenyl)-benzaldehyde 

Relevant academic research and scientific papers

MOF-808 as a recyclable catalyst for the photothermal acetalization of aromatic aldehydes

Metal-organic frameworks (MOFs) show promise for catalysis applications due to their porosity, high internal surface area, and structural adaptability. Typical acetylation reactions of aldehydes require elevated temperatures and excess alcohol to drive the reactions to completion. In this current work, MOF-808 is used as a heterogeneous catalyst for acetylation of aldehydes in methanol using a mild photothermal process. Optimized conditions gave 72% yield of 2-(dimethoxymethyl)naphthalene in the presence of 10 mol% MOF-808 at 45 °C using only a fluorescent lamp. MOF-808 can be recycled up to 5 times with no loss in catalytic activity. A proof-of-principle substrate scope demonstrates the potential utility for aromatic and aliphatic substrates.

Nickel-Catalyzed Chemoselective Acetalization of Aldehydes With Alcohols under Neutral Conditions

A molecularly defined NiII-complex catalyzing the chemoselective acetalization of aldehydes with alcohols under neutral conditions is reported. The reaction is general, efficient and showed a wide substrate scope (including aliphatic aldehydes) as well as excellent functional group tolerance. Reusability of the present nickel catalyst is also demonstrated.

Synthesis of 4-(Dibromomethyl)benzaldehyde by Catalytic Debromophosphoryl- and Phosphonyloxylation of 1,4-Bis(dibromomethyl)benzene with Phosphorus(IV) Acid Methyl Esters and Its Properties

A new procedure has been developed for the simultaneous preparation of terephthalaldehyde and 4-(dibromomethyl)benzaldehyde by catalytic debromophosphoryl- and phosphonyloxylation of 1,4-bis- (dibromomethyl)benzene with P(IV) acid methyl esters. The reaction of 4-(dibromomethyl)benzaldehyde with ortho esters in the presence of sulfuric acid gave the corresponding acetals, whereas in the presence of ZnCl2 terephthalaldehyde bis-acetals were formed. 4-(Dibromomethyl)benzaldehyde and its acetal were converted to methyl 4-(dibromomethyl)- and 4-(dimethoxymethyl)benzoates which were phosphorylated by the action of chlorophosphines, as well as by successive treatment with phosphorus(III) chloride and P(III) esters.

Preparation of acetals from aldehydes and alcohols under basic conditions

A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is facilitated by a sodium alkoxide along with a corresponding trifluoroacetate ester, utilizing formation of sodium trifluoroacetate as a driving force for acetal formation. The usefulness of this protocol is demonstrated by its orthogonality with various acid-sensitive protecting groups and by good compatibility with functional groups, delivering synthetically useful acetals complementarily to the synthesis under acidic conditions from aldehydes and alcohols.

Synthesis of aromatic aldehyde acetals from (dibromomethyl)arenes

Zinc chloride-catalyzed double debromoalkoxylation of (dibromomethyl)arenes on treatment with trialkyl orthoformates resulted in the corresponding aromatic aldehyde acetals. On the first step, α-brominated ether is formed, which undergoes the second debro

Effect of the Catalyst Nature on the Structure of Products of the Reaction of 4-(Dibromomethyl)Benzaldehyde with Trialkyl Orthoformates

Reactions of 4-(dibromomethyl)benzaldehyde with trialkyl orthoformates in the presence of both Br?nsted (H2SO4) and Lewis (ZnCl2) acids involved acetalization of the aldehyde group. In the first case, the corresponding acetal is formed as the only product, whereas in the second case the reaction is accompanied by transformation of the dibromomethyl group to give terephthalaldehyde and its mono- and bis-acetals.

An efficient and versatile procedure for the synthesis of acetals from aldehydes and ketones catalyzed by lithium tetrafluoroborate

Acetals are obtained in good to excellent yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of a catalytic amount of lithium tetrafluoroborate. Due to the mild reaction conditions, this method is compatible with acid-sensitive substrates.

Efficient acetalisation of aldehydes catalyzed by titanium tetrachloride in a basic medium

The acetalisation of aliphatic and aromatic aldehydes is achieved in a basic medium by using catalytic amount of Ti(IV) chloride in MeOH in the presence of NH3 or Et3N. The present protocol shows many advantages over the well known base or acid catalysis: in fact, in contrast to base-promoted acetalisation, aldehydes with electron-rich carbonyl groups react easily, enolizable aldehydes do not undergo aldol condensation and, in contrast to acid-catalysis, migration of the double bond does not occur in the preparation of α,β-unsaturated acetals.

A novel approach to the synthesis of benzoic and cinnamic acid derivatives with nor-isoprenoid substituents

A novel strategy for the synthesis of 4-(nor-polyprenyl)-substituted benzoic acids and their esters of the general formula 1 as well as their vinylogs of the type 2, based on the use of terephthalic aldehyde (3) and its tetramethyl acetal (13), is elaborated.The carbonyl groups in dialdehydes 3 and 12 can be selectively involved in the reaction sequences leading to the introduction of both aliphatic and functional substituents in positions 1 and 4 of the benzene ring.