Hydrochloric Acid → 4,4'-Didocosyloxy-benzophenone

HRID 573969

Reaction equation

O[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.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].[C:40](=[O:43])([O-])[O-].[K+].[K+].Cl>O.CN(C=O)C>[CH2:18]([O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([O:43][CH2:40][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:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1)[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: 80 °C

Procedure

To 4,4′-dihydroxy-benzophenone (8.2 g, 38.3 mmol) and 1-bromodocosane (31.3 g, 80.4 mmol) were added DMF (300 mL) and potassium carbonate (15.9 g, 115 mmol), and the mixture was stirred at 80° C. for 6.5 hr. After confirmation of the disappearance of the monoalkylated compound, the reaction mixture was ice-cooled, and 1N hydrochloric acid (300 mL) and water (150 mL) were slowly added to the thoroughly-stirred mixture. The slurry was filtered, and the obtained crystals were washed with water and methanol to give the title compound (28.3 g, 34.1 mmol, 89%).

Workup

temperaturecooled
filtrationThe slurry was filtered
washthe obtained crystals were washed with water and methanol

Sources & evidence

ORD record: ord-4a4eaa8aafdf4a3f9958ddec4998c56a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029528B2

Linked notes

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