66049-31-8

Basic information

• Product Name: 1-Naphthalenol, 3,4-dihydro-, benzoate
• CAS NO: 66049-31-8
• Molecular Formula: C17H14O2
• Molecular Weight: 250.297
• Mol File: 66049-31-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Naphthalenol, 3,4-dihydro-, benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Naphthalenol, 3,4-dihydro-, benzoate(66049-31-8)
• EPA Substance Registry System: 1-Naphthalenol, 3,4-dihydro-, benzoate(66049-31-8)

Safety Data

• Hazardous Substances Data: 66049-31-8(Hazardous Substances Data)

Upstream product

• 455-32-3 benzoyl fluoride 
• 38858-72-9 1-trimethylsiloxy-3,4-dihydronaphthalene 
• 93-97-0 benzoic acid anhydride 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 

Downstream Products

• 216099-55-7 (R,R)-1-(benzoyloxy)-1,2-epoxytetrahydronaphthalene 

Relevant articles and documents

DMAP-organocatalyzed O-silyl-O-(or C-)-benzoyl interconversions by means of benzoyl fluoride

A mild and efficient transprotection of alcohols from silyl ethers 1a-f to benzoates 2a-f is reported in fair to good yields (50-98%). This silyl-acyl exchange reaction proceeds readily in acetonitrile at room temperature in the presence of benzoyl fluoride and DMAP as an acyl transfer catalyst. A two-step 'one-pot' DMAP-catalyzed silylcyanation-transprotection sequence which gives the corresponding O-benzoyl cyanohydrines 2g-l in high yields (72-98%) from various benzaldehyde and ketone derivatives is also reported. This original organocatalytic acyl transfer process was also found to be effective in the O-benzoylation of trimethysilyl enolates 1m-o, providing enol esters 2m-o. Lastly, the potential of this strategy is also illustrated by a DMAP-mediated Claisen condensation between ketene silyl acetals 1p-r and benzoyl fluoride. Georg Thieme Verlag Stuttgart.

Enantioselective synthesis and stereoselective rearrangements of enol ester epoxides

Enol esters can be epoxidized with high enantioselectivities using the fructose-derived chiral ketone 1 as catalyst and Oxone as oxidant. A detailed study of enantiomerically enriched enol ester epoxides has revealed that the acid-catalyzed rearrangement can proceed through two distinct pathways, one with retention of configuration and the other with inversion. The competition between the two pathways is highly dependent upon the nature of the acid catalyst. A strong acid favors retention of configuration and a weak acid favors inversion of configuration. Under thermal conditions, these epoxides rearrange highly stereoselectively with inversion of configuration. Either enantiomer of an α-acyloxy ketone can be formed from one enantiomer of an enol ester epoxide by judicious choice of reaction conditions.