Potassium Carbonate → 14-(2,5-Dimethoxyphenoxy)tetradecan-1-ol

HRID 1367774Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33].[Cl-].[NH4+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[O:11][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33]

Participants

Conditions

Temperature: 56 °C

Procedure

2,5-Dimethoxyphenol (287.1 mg) was dissolved in 30 ml of acetone, and to this solution, potassium carbonate and a solution of 14-bromotetradecan-1-ol (599.5 g) in 2 ml of acetone were added. The reaction mixture was stirred at reflux temperature (56° C.) for 24 hours, and then neutralized with saturated ammonium chloride solution. It was then extracted three times with diethyl ether. The organic layer was washed with saline solution and dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure. Purification of the residue by silica gel chromatography (eluting with dichloromethane) gave 14-(2,5-dimethoxyphenoxy)tetradecan-1-ol as white crystals at a 65% yield.

Workup

extractionIt was then extracted three times with diethyl ether
washThe organic layer was washed with saline solution
dry with materialdried over magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customPurification of the residue
washby silica gel chromatography (eluting with dichloromethane)

Sources & evidence

ORD record: ord-22ea968327f04f39a6e578338de82178
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893304B2

Reaction notes

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