26431-13-0

Basic information

• Product Name: 3-Methyl-2-methylene-3-buten-1-ol
• Synonyms: 3-Methyl-2-methylene-3-buten-1-ol
• CAS NO: 26431-13-0
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.14
• Mol File: 26431-13-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Methyl-2-methylene-3-buten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-methylene-3-buten-1-ol(26431-13-0)
• EPA Substance Registry System: 3-Methyl-2-methylene-3-buten-1-ol(26431-13-0)

Safety Data

• Hazardous Substances Data: 26431-13-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 101, p. 1623, 1979 DOI: 10.1021/ja00500a058

Upstream product

• 34485-82-0 2,3-dimethyl-3,4-epoxy-1-butene 
• 6802-75-1 diethyl isopropylidenemalonate 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 463-49-0 1,2-propanediene 
• 593-71-5 Chloroiodomethane 
• 920-46-7 Methacryloyl chloride 

Downstream Products

• 186704-15-4 dibenzyl (R)-2-hydroxy-2-(hydroxymethyl)-3-methylbut-3-enylphosphonate 
• 186704-12-1 ((S)-2-Hydroxy-2-hydroxymethyl-3-methyl-but-3-enyl)-phosphonic acid dibenzyl ester 
• 186704-13-2 ((S)-2-Hydroxy-2-hydroxymethyl-3-oxo-butyl)-phosphonic acid dibenzyl ester 
• 186704-16-5 ((R)-2-Hydroxy-2-hydroxymethyl-3-oxo-butyl)-phosphonic acid dibenzyl ester 

Relevant articles and documents

REACTION OF ALLENE WITH WATER CATALYZED BY PALLADIUM(0) IN THE PRESENCE OF CARBON DIOXIDE.

A novel reaction involving allene and water took place using palladium(0)-triphenylphosphine as a catalyst in the presence of carbon dioxide to yield 3-methyl-2-methylene-3-buten-1-ol, selectively. A related reaction of allene with methanol or ethanol was found to occur without carbon dioxide.

Facile One-pot Transformation of Carboxylic Acid Chlorides into 2-Substituted Allyl Alcohols or Epichlorohydrins

Treatment of carboxylic acid chlorides (1) with chloromethyl-lithium generated in-situ (1:2 molar ratio) in the presence of lithium iodide leads, after hydrolysis, to the corresponding homologated 2-substituted allyl alcohols (2).When the same reaction is carried out using iodide-free butyl-lithium, instead of methyl-lithium-lithium iodide, the corresponding 2-substituted epichlorohydrines (5) are formed.

Palladium-Catalyzed Reaction of 1,3-Diene Monoepoxides with β-Keto Acids. Allylic Alkylation and Isomerization of 1,3-Diene Monoepoxides

Tetrakis(triphenylphosphine)palladium catalyzed the decarboxylative allylic alkylation of 1,3-diene monoepoxides with β-keto acids at ambient temperature to produce keto allylic alcohols in moderate to good yields. 1,3-Diene monoepoxides employed in this reaction were 3,4-epoxy-4-methyl-1-butene (2), 3,4-epoxy-2-methyl-1-butene (3), 4,5-epoxy-2-hexene (4), and 3,4-epoxy-1-pentene (5).As β-keto acids, 1-oxocyclohexane-2-carboxylic acid, benzoylacetic acid (1), and 1,3-acetonedicarboxylic acid were used.The allylic alkylation of 1,3-diene monoepoxide took place regioselectively at the allylic carbon atom distal the hydroxyl group .The stereochemistry of the resultant carbon-carbon double bond was predominantly to exclusively E.On the contrary, 3,4-epoxy-2,3-dimethyl-1-butene (6), 4,5-epoxy-2,5-dimethyl-2-hexene (7), and 3,4-epoxy-1-cyclohexene (8) took a different course of the reaction to undergo the palladium-catalyzed isomerization.The isomerization of 6 and 7 was accelerated by 1, but that of 8 was not.The effect of the structure of 1,3-diene monoepoxides upon the reaction course and the role of β-keto acid in the isomerization were discussed.