1-Bromooctane → HCID 54448652, compound

HRID 846493Notes

Reaction equation

HRID 846493 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:18]=[CH:17][C:16]=1[OH:28].[CH2:29](Br)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].C(=O)([O-])[O-].[K+].[K+]>[Cu].CN(C=O)C>[CH2:29]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[C:15]1[CH:20]=[C:19]([CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:18]=[CH:17][C:16]=1[OH:28])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 21734062HCID 21734062, compound

Product 1

HCID 54448652HCID 54448652, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

To 5 ml of a DMF solution containing 200 mg (0.5181 mmol) of 2,2'-dihydroxy-5,5'-bis (3-methoxycarbonylpropyl) biphenyl and 0.895 ml (5.181 mmol) of octyl bromide, there were added 85.8 mg (0.6217 mmol) of anhydrous potassium carbonate and a small amount of copper powder and the resulting mixture was agitated for 5 hours at room temperature. The reaction mixture was filtered by suction through Celite to remove the solid matter and the filtrate was washed with ethyl acetate. After the solvent in the filtrate was evaporated off under reduced pressure, the evaporated residue was dissolve din chloroform. This solution was washed with dilute hydrochloric acid, dilute aqueous sodium bicarbonate, water and aqueous sodium chloride solution in this sequence and was dried by adding anhydrous sodium sulfate. The residue obtained after the solvent had been evaporated off was purified by silica gel column chromatography (with 15 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 100/1) to obtain 236 mg (0.4738 mmol, 91%) of 2-octyloxy-2'-hydroxy-5,5'-bis (3-methoxycarbonylpropyl) biphenyl as an oily product. 1H-NMR (CDCl3) δ (ppm): 0.87 (3H, t, CH3), 1.0-2.2 (16H, m, 8CH2), 2.36 (4H, t, 2CH2), 2.65 (4H, t, 2CH2), 3.66 (6H, s, 2CH3), 4.01 (2H, t, CH2), 6.61 (1H, s, OH), 6.8-7.3 (6H, m, arom-H) MS (FAB): 497 (M-H)-

Workup

  1. filtrationThe reaction mixture was filtered by suction through Celite
  2. customto remove the solid matter
  3. washthe filtrate was washed with ethyl acetate
  4. customAfter the solvent in the filtrate was evaporated off under reduced pressure
  5. dissolutionthe evaporated residue was dissolve din chloroform
  6. washThis solution was washed with dilute hydrochloric acid, dilute aqueous sodium bicarbonate, water and aqueous sodium chloride solution in this sequence
  7. customwas dried
  8. additionby adding anhydrous sodium sulfate
  9. customThe residue obtained after the solvent
  10. customhad been evaporated off
  11. customwas purified by silica gel column chromatography (with 15 g of WAKO-gel C-200, eluent: toluene and toluene/ethyl acetate of 100/1)

Sources & evidence

ORD record
ord-48787e090db842099bd8f540019aecda
Source dataset
uspto-grants-1992_08
Patent number
US05136090

Reaction notes

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