Potassium Iodide → HCID 86623124, compound

HRID 536079Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

2-Chloroethyl methyl ether (4.63 mL, 50.7 mmol) was added dropwise to a mixture of 2,3-dihydroxybenzaldehyde (7.0 g, 50.7 mmol), potassium iodide (8.41 g, 50.69 mmol) and potassium carbonate (7.71 g, 55.8 mmol) in DMF (80 mL). The resulting mixture was stirred at r.t. under a nitrogen atmosphere for two days and at 70° C. for two days. The reaction mixture was partitioned between saturated ammonium chloride (aq.) and CH2Cl2. The water phase was re-extracted with CH2Cl2 and the combined organic phases were washed with brine, dried (Na2SO4) and evaporated onto silica. Purification by flash column chromatography (heptane/ethyl acetate gradient; 0 to 30% ethyl acetate) yielded a crude oil which was further purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 40% ethyl acetate) to yield the title compound (3.13 g, 31%) as an oil.

Workup

customThe reaction mixture was partitioned between saturated ammonium chloride (aq.) and CH2Cl2
extractionThe water phase was re-extracted with CH2Cl2
washthe combined organic phases were washed with brine
dry with materialdried (Na2SO4)
customevaporated onto silica
customPurification by flash column chromatography (heptane/ethyl acetate gradient; 0 to 30% ethyl acetate)
customyielded a crude oil which
customwas further purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 40% ethyl acetate)

Sources & evidence

ORD record: ord-3faa3e8d863a4a1a96332f6a4ad33303
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859568B2

Reaction notes

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