2-Methoxynaphthalene → HCID 67674172, compound

HRID 1290274Notes

Reaction equation

HRID 1290274 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.[C:17]([O:22][CH2:23][CH3:24])(=[O:21])[C:18]([CH3:20])=[O:19]>[N+](C)([O-])=O>[OH:19][C:18]([C:7]1([O:6][CH3:5])[CH:16]=[CH:15][C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:8]1)([CH3:20])[C:17]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 71192-MethoxynaphthaleneHCID 12041Ethyl pyruvateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67674172HCID 67674172, compound

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

Aluminium chloride (162 g, 12,2 mmol) was added in 3 portions to a solution of 2-methoxynaphthalene (1,28 g, 8,09 mmol) in nitromethane (20 mL) at 5° C. Ethyl pyruvate (1,41 g, 12,2 mmol) in nitromethane (10 mL) was added over 1 hour at this temperature. The reaction was allowed to proceed for 1 hour and warmed to 20° C. for 2 hours. Ethyl 2-hydroxy-2-(6-methoxynaphth-6-yl)propionate was formed with a selectivity of 16% at 52% conversion of the starting material.

Sources & evidence

ORD record
ord-6dcde557826046d486be4d2c4ca8d1fb
Source dataset
uspto-grants-1998_05
Patent number
US05750764

Reaction notes

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