Acetic Anhydride → 2-Methoxynaphthalene

HRID 1290277Notes

Reaction equation

HRID 1290277 reaction equation
O[C:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]=1)([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(OC(=O)C)(=O)C>[Pd].C1(C)C=CC=CC=1>[CH3:20][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:18]=[CH:17]2.[CH3:20][O:19][C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[CH:9][CH:10]=2)[CH:15]=1

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 10858682HCID 10858682, compound

Product 2

HCID 71192-MethoxynaphthaleneHCID 2732945ethyl 2-(6-methoxynaphthalen-2-yl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Ethyl 2-hydroxy-2-(6-methoxynaphth-2-yl)propionate (7,5 g, 27,3 mmol), acetic anhydride (6,14 g, 60,2 mmol), toluene (37 ml) and palladium catalyst (5% on carbon, 0,75 g) were heated (140° C.) under a hydrogen atmosphere (10 bar) for 14 hours. Ethyl 2-(6-methoxynaphth-2-yl)propionate was formed with a selectivity of 92% at a 2-methoxynaphthalene conversion of 60%.

Sources & evidence

ORD record
ord-e8016fd9bd834cd99440a28d1e80058b
Source dataset
uspto-grants-1998_05
Patent number
US05750764

Reaction notes

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