Potassium Hydroxide → 2-(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)ethyl-4-methoxybenzene

HRID 2227102Notes

Reaction equation

[CH3:1][C:2]([CH3:23])=[CH:3][CH2:4][CH2:5][C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=O)[CH2:8][CH:7]=1.[OH-].[K+].O.NN>C(O)COCCO>[CH3:1][C:2]([CH3:23])=[CH:3][CH2:4][CH2:5][C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:8][CH:7]=1

Participants

Conditions

Temperature: 125 °C

Procedure

To a solution of ketone 2E (R=4-Methyl-3-pentenyl) (10 g) in diethylene glycol (30 mL) is added potassium hydroxide (4.3 g) and hydrazine hydrate (4.5 mL). The solution is sequentially heated to 100° C., 125° C., and 150° C., all for 30 minutes each, then cooled to room temperature. The reaction mixture is extracted between ethyl ether and water, and the combined organic layers are washed with brine and dried over magnesium sulfate. The solution is concentrated in vacuo, and the product is purified by silica gel filtration using 20:1 hexanes:ethyl acetate as an eluent.

Workup

temperature150° C., all for 30 minutes each, then cooled to room temperature
extractionThe reaction mixture is extracted between ethyl ether and water
washthe combined organic layers are washed with brine
dry with materialdried over magnesium sulfate
concentrationThe solution is concentrated in vacuo
filtrationthe product is purified by silica gel filtration

Sources & evidence

ORD record: ord-9beabb29ff9a402cb93a67449f2ebe89
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06413448B1

Reaction notes

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