1-Bromododecane → HCID 18915764, compound

HRID 1292585Notes

Reaction equation

HRID 1292585 reaction equation
O[C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[C:12]([OH:17])[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][CH3:30].[C:31](=[O:34])([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CN(C)C(=O)C.[I-].[K+]>[OH:17][C:12]1[CH:13]=[C:14]([O:16][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:15]=[C:2]([O:34][CH2:31][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:4][CH2:3][CH2:2][CH2:15][CH3:14])[C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

7

Reactant 3

HCID 89191-BromododecaneHCID 11430Potassium CarbonateHCID 77093Methanone, phenyl(2,4,6-trihydroxyphenyl)-

Product 1

HCID 18915764HCID 18915764, compoundYield 72.3%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4.5 g (20 mmol) of 2,4,6-trihydroxybenzophenone, 9.8 g (40 mmol) of 1-bromododecane, 2.7 g (20 mmol) of potassium carbonate and 30 mg (0.2 mmol) of potassium iodide in 50 ml of toluene and 20 ml of N,N-dimethylacetamide is stirred at 110° C. for 7 h. The reaction mixture is cooled and then neutralized with 10% HCI. The organic solution is washed with water and then with saturated sodium chloride solution. The residue which remains after drying over MgSO4, filtering and concentrating by evaporation is purified by chromatography over silica gel (toluene/hexane 3:2). The product is recrystallized from isopropyl alcohol. 4.1 g of the compound are obtained as pale yellow crystals having a melting point of 37°-38° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washThe organic solution is washed with water
  3. dry with materialafter drying over MgSO4
  4. filtrationfiltering
  5. concentrationconcentrating by evaporation
  6. customis purified by chromatography over silica gel (toluene/hexane 3:2)
  7. customThe product is recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-2d483a23a9cb4d5f8cc1d4f309d462cb
Source dataset
uspto-grants-1998_05
Patent number
US05756793

Reaction notes

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