2-Methoxynaphthalene → HCID 67674172, compound

HRID 1290272Notes

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]>ClCCl>[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

Conditions

Temperature: -20 °C

Procedure

Aluminium chloride (2,49 g, 18,7 mmol) was added in 2 portions to a solution of 2-methoxynaphthalene (1,97 g, 12,5 mmol) in dichloromethane (15 mL) at 5° C. The red solution was cooled to -20° C. and the reaction vessel was evacuated to a pressure of 160 mbar. Ethyl pyruvate (2,17 g, 18,7 mmol) in dichloromethane (pre-cooled, 5 mL) was added over 5 minutes and the temperature was further reduced to -40° C. The reaction was allowed to proceed for 2 hours, at which time the system was opened to the atmosphere and poured on to ice. Ethyl 2-hydroxy-2-(6-methoxynaphth-6-yl)propionate was formed with a selectivity of 35% at 62% conversion of the starting material.

Workup

customthe reaction vessel was evacuated to a pressure of 160 mbar
customwas further reduced to -40° C
additionpoured on to ice

Sources & evidence

ORD record: ord-97f2a7032ba144f082803d93da79f8e2
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750764

Reaction notes

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