76337-19-4

Basic information

• Product Name: Cyclohexene, 1-[(ethenyloxy)methyl]-3,3-dimethyl-
• CAS NO: 76337-19-4
• Molecular Formula: C11H18O
• Molecular Weight: 166.263
• Mol File: 76337-19-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Cyclohexene, 1-[(ethenyloxy)methyl]-3,3-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexene, 1-[(ethenyloxy)methyl]-3,3-dimethyl-(76337-19-4)
• EPA Substance Registry System: Cyclohexene, 1-[(ethenyloxy)methyl]-3,3-dimethyl-(76337-19-4)

Safety Data

• Hazardous Substances Data: 76337-19-4(Hazardous Substances Data)

Upstream product

• 41641-14-9 1-hydroxymethyl-3,3-dimethyl-cyclohex-1-ene 
• 854717-42-3 2-Isobutoxymethylene-6,6-dimethylcyclohexanone 
• 76337-17-2 2-formyl-6,6-dimethylcyclohexanone 
• 583-60-8 2-Methylcyclohexanone 
• 61188-00-9 (Z)-6-(hydroxymethylene)-2,2-dimethylcyclohexanone 
• 76337-18-3 3,3-Dimethylcyclohex-1-ene-1-carbaldehyde 
• 109-92-2 ethyl vinyl ether 

Downstream Products

• 547-15-9 2-(6',6'-Dimethyl-2'-methylenecyclohexyl)ethanal 
• 67656-40-0 5-(6',6'-dimethyl-2'-methylenecyclohexyl)-3-hydroxy-3-methyl-pent-1-ene 
• 35316-47-3 trans-8-Monocyclofarnesol 
• 13720-13-3 4-(6',6'-dimethyl-2'-methylenecyclohexyl)butan-2-ol 
• 76337-22-9 3-(6',6'-dimethyl-2'-methylenecyclohexyl)propan-1-al 
• 76337-20-7 1-Methoxy-3-(6',6'-dimethyl-2'-methylenecyclohexyl)propene-1 
• 76337-21-8 1,1-Ethylenedioxy-3-(6',6'-dimethyl-2'-methylenecyclohexyl)propane 
• 76337-23-0 5-(6',6'-dimethyl-2'-methylenecyclohexyl)-3-methyl-pent-2-enylacetate 
• 92154-89-7 1,1-Dimethyl-2-(β-hydroxy-butyl)-3-methylen-cyclohexan 
• 92037-12-2 1,1-Dimethyl-3-methylen-2-(β-hydroxypropyl)-cyclohexan 
• 69924-94-3 (+/-)-(R^*R^*)-α-<(2,2-dimethyl-6-methylenecyclohexyl)methyl>furan-3-methanol 
• 69924-97-6 (+/-)-(αRS,1'SR,2'RS)-α-<(2'-hydroxy-2',6',6'-trimethylcyclohexyl)methyl>furan-3-methanol 
• 69924-97-6 (+/-)-(αRS,1'RS,2'SR)-α-<(2'-hydroxy-2',6',6'-trimethylcyclohexyl)methyl>furan-3-methanol 
• 69924-97-6 (+/-)-(αRS,1'RS,2'RS)-α-<(2'-hydroxy-2',6',6'-trimethylcyclohexyl)methyl>furan-3-methanol 

Relevant articles and documents

New Synthesis of γ-Homocyclogeranial, γ-Dihydroionone and Their Derivatives

A new and efficient synthesis of γ-homocyclogeranial (4), γ-dihydroionone (3) and their derivatives, 5, 6, 7 and 8, volatile components of ambergris, is described.Their compounds were synthesized via Claisen rearrangement of (3,3-dimethylcyclohexenyl)methyl vinyl ether (14).

Synthesis of trans-γ-Monocyclofarnesol

The starting material, 2-formyl-6,6,dimethylcyclohexanone (II) in the synthesis of the title compound, is converted into the corresponding 2-isobutoxymethylene-6,6-dimethylcylohexanone (III).Reduction of (III) with LAH followed by treatment with 50percent sulphuric acid gives the α,β-unsaturated aldehyde (IV).LAH reduction of IV yields 1-hydroxymethyl-3,3-dimethylcylohex-1-ene (V) which on mercuric acetate catalysed transetherification with ethyl vinyl ether affords the vinyl ether (VI).Claisen rearragement of VI under an inert atmosphere furnishes 2-(6',6'-dimethyl-2'-methylenecylohexyl)ethanal (VII).Aldehyd VII on Wittig reaction with methoxymethylenetriphenylphosphorane provides the ether (VIII) which is readily converted into the ketal (IX) on treatment with ethylene glycol in the presence of catalytic amount of PTS in dry benzene.Deketalisation of IX with PTS in aq. acetone gives the aldehyde (X) which on Grignard reaction with methylmagnesium iodide furnishes 4-(6',6'-dimethyl-2'-methylenecylohexyl)butan-2-ol (XI).Oxidation of XI with pyridinium chlorochromate in anhydrous methylene chloride yields the ketone (XII) which when subjected to Grignard reaction with vinylmagnesium bromide in dry THF provides the vinylic alcohol (XIII).Treatment of XIII with acetic anhydride and glacical acetic acid in the presence of PTS furnishes the allylic acetate (XIV) which on refluxing with methanolic potassium hydroxide in the presence of a little water gives trans-γ-monocyclofarnesol (I).