97382-22-4

Basic information

• Product Name: 2-hydroxymethyl-2-adamantyl-1-adamantanecarboxylate
• Synonyms: 2-hydroxymethyl-2-adamantyl-1-adamantanecarboxylate
• CAS NO: 97382-22-4
• Molecular Weight: 344.494
• Mol File: 97382-22-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-hydroxymethyl-2-adamantyl-1-adamantanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxymethyl-2-adamantyl-1-adamantanecarboxylate(97382-22-4)
• EPA Substance Registry System: 2-hydroxymethyl-2-adamantyl-1-adamantanecarboxylate(97382-22-4)

Safety Data

• Hazardous Substances Data: 97382-22-4(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 2094-74-8 1-Adamantanecarbaldehyde 
• 77418-99-6 1-adamantyl trifluoromethanesulfonate 
• 281-23-2 adamantane 
• 25236-60-6 1-adamantyl methanesulfonate 
• 768-90-1 1-Adamantyl bromide 

Relevant articles and documents

REACTION OF 1-ADAMANTYL CATION WITH CARBON MONOXIDE IN THE PRESENCE OF ADAMANTANE AND TRIFLUOROMETHANESULFONIC ACID: A CONVENIENT ROUTE TO 3,4-HOMOADAMANTANEDIOL

The carbonylation of the 1-adamantyl cation with carbon monoxide in carbon tetrachloride at atmospheric pressure in the presence of trifluoromethanesulfonic acid (triflic acid) and adamantane affords 3-hydroxy-4-homoadamantyl 1-adamantanecarboxylate (2) in 70percent yield under appropriate conditions.Among various 1-adamantyl cation precursors tested, 1-adamantyl trifluoromethanesulfonate (triflate) and methanesulfonate (mesylate) have given the best, comparable results.As to the acid catalyst, fluorosulfonic acid is less effective than triflic acid, and 100percent sulfuric acid a nd methanesulfonic acid are completely ineffective to produce 2.It is recommended to use five mol each of triflic acid and adamantane per mol of 1-adamantyl mesylate or triflate.This reaction proceeds via the addition of the 1-adamantanecarbynol cation to 1-adamantanecarbaldehyde, a transient intermediate, followed by the Wagner-Meerwein rearrangement.The hydroxy ester 2 is easily converted into 3,4-homoadamantanediol which is a promising starting material for 3,4-bifunctional homoadamantane derivates.