Ethanol → ethyl 2-(6-methoxynaphthalen-2-yl)propanoate

HRID 1290278Notes

Reaction equation

HRID 1290278 reaction equation
[H][H].O[C:4]([C:11]1(OC)[CH:20]=[CH:19][C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:12]1)([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH2:23]([OH:25])C>[Pd]>[CH3:23][O:25][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[C:11]([CH:4]([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:20]=[CH:19]2

Participants

5

Reactant 3

HCID 702EthanolHCID 67674172HCID 67674172, compoundHCID 178418361HCID 178418361, compound4×

Product 1

HCID 2732945ethyl 2-(6-methoxynaphthalen-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
160 °C

Procedure

Ethanol (48 g) and palladium catalyst (5% palladium on carbon, 0,12 g) were stirred under a hydrogen atmosphere (10 bar) for 1 hour. The hydrogen was released and ethyl 2-hydroxy-2-(6-methoxynaphth-6-yl)propionate (12,0 g, 43,8 mmol) was added. Hydrogen was charged to the reactor and the vessel was warmed to 160° C. (hydrogen pressure 20 bar). The reactor was stirred at 160° C. for 6 hours and the hydrogen was released. Ethyl 2-(6-methoxynaphth-2-yl)propionate was formed with a selectivity of 35% at 40% conversion of the starting material.

Sources & evidence

ORD record
ord-6a29cf98951c49c7b5925152479dd0fc
Source dataset
uspto-grants-1998_05
Patent number
US05750764

Reaction notes

Loading…