1-Bromopentane → 3-Methyl-1-pentyloxynaphthalene

HRID 850421Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([OH:12])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH3:23]>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([O:12][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 90 °C

Procedure

The crude product of 3-methylnaphthalen-1-ol, dimethylformamide (DMF, 20 ml), potassium carbonate (3 g, 21.7 mmol) and pentyl bromide (4.0 ml, 32.3 mmol) were mixed in a reaction vessel replaced with argon, and this solution was stirred at 90° C. for 3 hours. DMF was evaporated under reduced pressure, and water (20 ml) was added. The aqueous layer was extracted with ethyl acetate (20 ml) 3 times. The organic layer was washed with saturated brine (20 m1l) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=100/0-50/1) to give 3-methyl-1-pentyloxynaphthalene (827 mg, 12% in 3 steps) as a colorless oil.

Workup

customDMF was evaporated under reduced pressure, and water (20 ml)
additionwas added
extractionThe aqueous layer was extracted with ethyl acetate (20 ml) 3 times
washThe organic layer was washed with saturated brine (20 m1l)
dry with materialdried over anhydrous magnesium sulfate
filtrationThe drying agent was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=100/0-50/1)

Sources & evidence

ORD record: ord-659bfe8676834ed0a5eea9c78d3894c2
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017919

Reaction notes

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