Hydrochloric Acid → 2,3,4-Trioctadecanoxybenzophenone

HRID 1754815Notes

Reaction equation

HRID 1754815 reaction equation
[OH:1][C:2]1[C:15]([OH:16])=[C:14](O)[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].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][CH2:33][CH2:34][CH2:35][CH3:36].[C:37](=[O:40])([O-])[O-].[K+].[K+].Cl>C(Cl)(Cl)Cl.CN(C=O)C>[CH2:19]([O:1][C:2]1[C:15]([O:16][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][CH3:19])=[C:14]([O:40][CH2:37][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][CH3:19])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[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][CH3:36]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 70837Alizarin Yellow A

Product 1

HCID 595103512,3,4-TrioctadecanoxybenzophenoneYield 93%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 2,3,4-trihydroxybenzophenone (1.60 g, 6.95 mmol) was added DMF (30 ml), 1-bromooctadecane (7.3 g, 21.9 mmol) and potassium carbonate (4.32 g, 31.3 mmol), and the mixture was stirred at 80° C. overnight. The reaction mixture was cooled to room temperature, chloroform (100 ml) was added, and 1N hydrochloric acid (30 ml) was further added dropwise. After stirring, the mixture was partitioned, and the organic layer was washed with 1N hydrochloric acid (30 ml) and water (30 ml). The organic layer was evaporated under reduced pressure, and the residue was washed with methanol (30 ml). The obtained precipitate was slurry washed with methanol (45 ml) to give 2,3,4-trioctadecanoxybenzophenone (6.35 g, 6.43 mmol, yield 93%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringAfter stirring
  3. customthe mixture was partitioned
  4. washthe organic layer was washed with 1N hydrochloric acid (30 ml) and water (30 ml)
  5. customThe organic layer was evaporated under reduced pressure
  6. washthe residue was washed with methanol (30 ml)
  7. washwashed with methanol (45 ml)

Sources & evidence

ORD record
ord-2527f7e7e8d5487190729e30994c2455
Source dataset
uspto-grants-2015_10
Patent number
US09169187B2

Reaction notes

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