862387-17-5

Basic information

• Product Name: methyl 4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]benzoate
• Synonyms: methyl 4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]benzoate
• CAS NO: 862387-17-5
• Molecular Weight: 300.398
• Mol File: 862387-17-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: methyl 4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]benzoate(862387-17-5)
• EPA Substance Registry System: methyl 4-[(hydroxy)(1,2,3,4,5-pentamethyl-2,4-cyclopentadienyl)methyl]benzoate(862387-17-5)

Safety Data

• Hazardous Substances Data: 862387-17-5(Hazardous Substances Data)

Upstream product

• 4045-44-7 1,2,3,4,5-pentamethylcyclopentadiene 
• 1571-08-0 methyl 4-formylbenzoate 

Downstream Products

• 4045-44-7 1,2,3,4,5-pentamethylcyclopentadiene 
• 1571-08-0 methyl 4-formylbenzoate 

Relevant articles and documents

Pentamethylcyclopentadienide in organic synthesis: Nucleophilic addition of lithium pentamethylcyclopentadienide to carbonyl compounds and carbon-carbon bond cleavage of the adducts yielding the parent carbonyl compounds

Lithium pentamethylcyclopentadienide (C5Me5Li, Cp*Li) reacted with aromatic aldehyde to provide the corresponding carbinol in excellent yield. The carbinol returns to the parent aldehyde and pentamethylcyclopentadiene upon exposure to acid or due to heating. Chlorodimethylaluminum is essential as an additive to attain the nucleophilic addition of Cp*Li to aliphatic aldehyde. The carbinol derived from aliphatic aldehyde returns to the parent aldehyde and pentamethylcyclopentadiene by the action of a catalytic amount of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ). The reversible addition/elimination of the Cp* group can represent a protection of aldehyde. Mechanistic details of the carbon-carbon bond cleavage are also disclosed.