1-Naphthol → HCID 53988552, compound

HRID 248128

Reaction equation

HRID 248128 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:12]([O:17][CH2:18][C@@H:19]1[O:21][CH2:20]1)(=[O:16])[CH2:13][CH2:14][CH3:15]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:12]([O:17][CH2:18][C@H:19]([OH:21])[CH2:20][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)(=[O:16])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 70051-NaphtholHCID 2724536(2R)-Oxiran-2-ylmethyl butanoate

Product 1

HCID 53988552HCID 53988552, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 144 g (1 mol) of 1-naphthol and 7.4 g (0.02 mol) of tetrabutylammonium iodide in 200 ml of toluene was added 144 g (1 mol) of (R)-glycidyl butyrate over a period of 15 min at a temperature of 120° C., and the mixture was kept at this temperature for a further 4 h. Conventional subsequent treatment of the reaction mixture gave the required compound as an oil, yield about 75%.

Sources & evidence

ORD record
ord-86e317ef3b474747a22b6fcc78057d05
Source dataset
uspto-grants-1993_05
Patent number
US05208333

Linked notes

Loading…