Potassium Iodide → HCID 69764959, compound

HRID 896725Notes

Reaction equation

[CH2:1]([O:17][C:18](=[O:28])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN1C(=O)CCC1.O>[CH2:1]([O:17][C:18](=[O:28])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][OH:36])=[CH:23][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 90 °C

Procedure

3-(4-Hydroxy-phenyl)-acrylic acid hexadecyl ester (4.8 g, 12.4 mmol) was dissolved in 100 ml of NMP. To this was added 6-chlorohexanol (2.19 g, 16 mmol), anhydrous potassium carbonate (1.7 g, 12 mmol) and a catalytic amount of potassium iodide. The reaction was stirred at 90° C. for 18 hours. Water was added to the cooled solution, which was subsequently extracted with 3×100 mls of ethyl acetate. The combined organics were washed with water (2×100 mls), water/brine (100 ml, 50:50) and brine solution and then dried over magnesium sulfate. The concentrated product was purified by silica gel chromatography eluting with 25% ethyl acetate in hexane to give 2.6 g white solid.

Workup

extractionwas subsequently extracted with 3×100 mls of ethyl acetate
washThe combined organics were washed with water (2×100 mls), water/brine (100 ml, 50:50) and brine solution
dry with materialdried over magnesium sulfate
customThe concentrated product was purified by silica gel chromatography
washeluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record: ord-d2c7eaeb460a4023a41f277e9ba3d8ce
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06919404B2

Reaction notes

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