42463-79-6

Basic information

• Product Name: Allyl(4-methylbenzyl) ether
• Synonyms: 1-Methyl-4-(2-propenyloxy)methylbenzene;Allyl(4-methylbenzyl) ether
• CAS NO: 42463-79-6
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 0
• Mol File: 42463-79-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Allyl(4-methylbenzyl) ether(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl(4-methylbenzyl) ether(42463-79-6)
• EPA Substance Registry System: Allyl(4-methylbenzyl) ether(42463-79-6)

Safety Data

• Hazardous Substances Data: 42463-79-6(Hazardous Substances Data)

Upstream product

• 589-18-4 4-Methylbenzyl alcohol 
• 107-18-6 allyl alcohol 
• 132907-18-7 3,6-dimethoxy-3,6-dimethylcyclohexa-1,4-diene 
• 104-81-4 4-Methylbenzyl bromide 
• 106-95-6 allyl bromide 

Downstream Products

• 1234780-54-1 (-)-(S)-1-[2-(allyloxy)-6-methylhept-5-en-2-yl]-4-methylbenzene 
• 1234780-57-4 (+)-(R)-1-[2-(allyloxy)-6-methylhept-5-en-2-yl]-4-methylbenzene 

Relevant articles and documents

Synthesis of (+)- and (-)-gossonorol and cyclisation to boivinianin B

The first enantioselective synthesis of gossonorol has been achieved in good overall yield and excellent enantioselectivity, demonstrating the utility of a novel approach to enantiopure tertiary benzylic alcohols. Epoxidation of enantiopure gossonorol followed by acid-catalysed cyclisation gave a diastereoisomeric mixture of boivinianin B, typical of the diastereoisomeric mixtures of this compound found in nature. Separation of the diastereoisomers and determination of their enantiopurity revealed that the stereochemical integrity of the benzylic alcohol of gossonorol had been preserved during the epoxidation/cyclisation reaction.

REACTIVITY OF 3,6-DIMETHOXY-3,6-DIMETHYLCYCLOHEXA-1,4-DIENE: NUCLEAR VERSUS BENZYLIC NUCLEOPHILIC SUBSTITUTION

The treatment of cis/trans-3,6-dimethoxy-3,6-dimethylcyclohexa-1,4-diene (ca. 1/1 mixture; easily prepared electrochemically in multigram scale from p-xylene) under acidic conditions (acetic, trifluoroacetic, sulfuric, or a Lewis acid) yields almost exclusively 2-methoxy-1,4-dimethylbenzene 4, through a trasposition reaction.The use of aqueous hydrochloric or hydrofluoric acid gives 2,5-dimethylphenol 12, and with hydrogen chloride a mixture of 2- and α-chloro-p-xylene (13, 14) is isolated.Different oxygen-, nitrogen-, and sulfur-containing nucleophiles (alcohols,thiols, or hydrazoic acid) react with 3 under acid catalysis giving the corresponding products resulting from a nuclear or/ and benzylic substitution on p-xylene (15 - 20).The reaction of compound 3 with organolithium reagents affords exclusively benzylic products 21 in a regiospecific manner.In all cases the mixtures of isomers are separated by column chromatography.The lithiation of compound 3 with lithium powder or lithium naphthalenide fails, giving p-xylene.A probable mechanism is proposed for the studied reactions.