2,4-Dihydroxybenzaldehyde → 2,4-Bis(docosyloxy)benzaldehyde

HRID 573963

Reaction equation

[OH:1][C:2]1[CH:9]=[C:8](O)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11](=[O:14])([O-])[O-].[K+].[K+].Br[CH2:18][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][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>CN(C)C=O>[CH2:18]([O:1][C:2]1[CH:9]=[C:8]([O:14][CH2:11][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])[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][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

Conditions

Temperature: 70 °C

Procedure

Under an argon atmosphere, 2,4-dihydroxybenzaldehyde (3.00 g, 21.7 mmol), potassium carbonate (30.0 g, 217 mmol) and 1-bromodocosane (17.3 g, 44.5 mmol) were added to dehydrating N,N-dimethylformamide (150 mL), and the mixture was stirred at 70° C. overnight. After completion of the reaction, the reaction mixture was poured into purified water (1 L), the mixture was stirred for 1 hr, and the precipitated solid was collected by filtration. The obtained solid was slurry-washed in methanol and filtered, and the obtained solid was dried under reduced pressure to give the title compound (16.3 g, 99.3%) as a white solid.

Workup

customAfter completion of the reaction
additionthe reaction mixture was poured
custominto purified water (1 L)
stirringthe mixture was stirred for 1 hr
filtrationthe precipitated solid was collected by filtration
washThe obtained solid was slurry-washed in methanol
filtrationfiltered
customthe obtained solid was dried under reduced pressure

Sources & evidence

ORD record: ord-0c9760cc24f8430eb4b095e72f324c88
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029528B2

Linked notes

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