Hydrochloric Acid → 1-(Cyclohex-1-en-1-yl)-3-methoxybenzene

HRID 1837180Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2(O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.O=S(Cl)Cl.N1C=CC=CC=1.Cl>C1COCC1>[C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 1L 3-neck RBF under argon was charged with crude 1-(m-methoxyphenyl)cyclohexanol (59.2 g, 287 mmol). To the flask was added 592 mL of dry THF. The reaction was cooled to 0° C., and to it was slowly added SOCl2 (58.6 mL, 803.6 mmol). After stirring for 10 minutes, pyridine (104 mL, 1.29 mol) was added slowly. The reaction mixture stirred slowly at 22° C. for 2 hours, and then it was cooled back to 0° C. 1N HCl (500 mL) was slowly added to the reaction. The layers were separated. The THF layer was dried (MgSO4), filtered, and concentrated in vacuo. The crude product was chromatographed using 100% hexane as eluent to provide 39.5 g (82%, 2 steps) of product. 1H NMR (CDCl3) δ1.72 (m, 2H), 1.83 (m, 2H), 2.24 (m, 2H), 2.45 (m, 2H), 3.86 (s, 3H), 6.18 (m, 1H), 6.83 (dd, J=8.1, 1.7 Hz, 1H), 6.98 (m, 1H), 7.03 (d, J=6.1 Hz, 1H), 7.27 (t, J=7.8 Hz, 1H).

Workup

stirringThe reaction mixture stirred slowly at 22° C. for 2 hours
temperatureit was cooled back to 0° C
customThe layers were separated
dry with materialThe THF layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was chromatographed
customto provide 39.5 g (82%, 2 steps) of product

Sources & evidence

ORD record: ord-f6061f52c0a1436aa657baa43c306194
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780891B2

Reaction notes

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