Potassium Iodide → HCID 71272497, compound

HRID 2204901Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[OH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

20.0 g (150 mmol) of (4-hydroxyphenyl)acetonitrile and 29.5 g (179 mmol) of 8-chlorooctan-1-ol are dissolved in 400 mL of N,N-dimethylformamide. 41.5 g (300 mmol) of potassium carbonate and 5.0 g (30 mmol) of potassium iodide are added and the suspension is heated to 80° C. After 48 h, the excess of potassium carbonate is filtered off and the resulting filtrate is poured to icy water. The aqueous layer is extracted twice with ethyl acetate. Combined organic layers are washed with brine and evaporated to dryness. The crude is purified twice on column chromatography (SiO2, Heptane/ethyl acetate: 7/3) and dried overnight at 40° C. 24.5 g of {4-[(8-hydroxyoctyl)oxy]phenyl}acetonitrile are obtained as a yellow solid (62% yield). This material proves chromatographically homogenous and displays spectral characteristics consistent with its assigned structure.

Workup

filtrationthe excess of potassium carbonate is filtered off
additionthe resulting filtrate is poured to icy water
extractionThe aqueous layer is extracted twice with ethyl acetate
washCombined organic layers are washed with brine
customevaporated to dryness
customThe crude is purified twice on column chromatography (SiO2, Heptane/ethyl acetate: 7/3)
customdried overnight at 40° C

Sources & evidence

ORD record: ord-9902c0f1977044d1b298d87435721eeb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09366906B2

Reaction notes

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