Potassium Iodide → Methyl 3-{4-[(6-hydroxyhexyl)oxy]phenyl}prop-2-enoate

HRID 1867775Notes

Reaction equation

[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)=[O:4].Cl[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN1C(=O)CCC1.O>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Methyl 4-hydroxy cinnamate (40 g, 225 mmol) was dissolved in 300 ml of NMP. 6-Chlorohexanol (269 mmol, 36.8 g), anhydrous potassium carbonate (37.2 g, 269 mmol) and a catalytic amount of potassium iodide were added. The batch was stirred at 90° C. for 32 hours. Water was added to the cooled solution, which was subsequently extracted with 3×200 mls of ethyl acetate. The combined organics were washed with 10% KOH (2×100 mls), brine solution and then dried over magnesium sulfate. The concentrated product was then recrystallized from a 1:1 mixture of ethyl acetate/hexane to give 45 g (72% yield) of an off-white solid.

Workup

extractionwas subsequently extracted with 3×200 mls of ethyl acetate
washThe combined organics were washed with 10% KOH (2×100 mls), brine solution
dry with materialdried over magnesium sulfate
customThe concentrated product was then recrystallized from a 1:1 mixture of ethyl acetate/hexane

Sources & evidence

ORD record: ord-2f6c65ca1bee4dd09ed03e0b7e9478ee
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07632875B2

Reaction notes

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