Hydrochloric Acid → HCID 11344349, compound

HRID 1760137Notes

Reaction equation

C([O:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[CH:9][CH:10]=2)[O:5]1)C.C(#N)C.Cl.[OH-].[Na+]>O>[OH:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[CH:9][CH:10]=2)[O:5]1

Participants

Conditions

Temperature: 60 °C

Procedure

A 500-milliliter egg plant type flask was charged with 5.14 g of 2-ethoxy-7-methoxychroman, 74 ml of acetonitrile and 25 ml of water, and 4.8 ml of a 35% hydrochloric acid aqueous solution was slowly added thereto dropwise at room temperature. The solution was stirred at 60° C. for 20 minutes, and then cooled to 20° C. The reaction solution was neutralized with 39 ml of a 5% sodium hydroxide aqueous solution, and the acetonitrile was removed by distillation in vacuo therefrom. The residue was extracted three times with 50 ml of ethyl acetate, and the organic layer was washed with water. Then, the ethyl acetate was removed by distillation in vacuo therefrom. The resulting residue was purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate 5:1) to obtain 3.60 g of a colorless liquid (yield 81%). Further, 0.77 g of 2-ethoxy-7-methoxychroman was recovered.

Workup

additionwas slowly added
customdropwise at room temperature
temperaturecooled to 20° C
customthe acetonitrile was removed by distillation in vacuo
extractionThe residue was extracted three times with 50 ml of ethyl acetate
washthe organic layer was washed with water
customThen, the ethyl acetate was removed by distillation in vacuo
customThe resulting residue was purified by silica gel column chromatography (solvent; n-hexane:ethyl acetate 5:1)

Sources & evidence

ORD record: ord-93aceed84b3c490cbd9d274ff20c028e
Source dataset: uspto-grants-2005_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06841183B2

Reaction notes

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