Potassium Carbonate → HCID 57560094, compound

HRID 1724115Notes

Reaction equation

HRID 1724115 reaction equation
[CH2:1]([O:11][C:12]1[CH:13]=[C:14]([OH:29])[CH:15]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Br:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]Br.C([O-])([O-])=O.[K+].[K+]>C1(=O)CCCCC1>[Br:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][O:29][C:14]1[CH:13]=[C:12]([O:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH:17]=[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 57560093HCID 57560093, compound

Product 1

HCID 57560094HCID 57560094, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 7967CyclohexanoneSolvent

Procedure

A mixture of 9 (2.70 g, 6.64 mmol), 1,6-dibromohexane (15.0 ml, 98.4 mmol), K2CO3 (2.29 g, 16.6 mmol) in cyclohexanone (50 ml) was heated for 16 h under reflux. The mixture was allowed to cool to RT, the inorganic salts are filtered off, followed by rinsing with acetone. The solvent and the excess 1,6-dibromohexan are distilled off in vacuo, and the residue is purified by means of column chromatography (silica gel, chloroform/petroleum ether 1:2). 2.62 g (69%) of compound 10 could be isolated in form of a light yellow oil. IR (film) 2895, 2810, 1575 cm−1; 1H-NMR (CDCl3) δ 6.05 (s, 3H), 3.94-3.86 superimposed signals (3.91, t, 6.4 Hz, 2H and 3.90, t, 6.7 Hz, 4H), 3.42 (t, 6.7 Hz, 2H), 1.95-1.83 (m, 2H), 1.81-1.69 (m, 6H), 1.52-1.21 (m, 32H), 0.88 (t, 6.8 Hz, 6H); MS (FD) m/z 571 (M+ for Br81), 569 (M+ for Br79). Anal. calc. for C32H57BrO3: C, 67.46; H, 10.08. Found C, 67.67; H, 10.12.

Workup

  1. temperaturewas heated for 16 h
  2. temperatureunder reflux
  3. filtrationthe inorganic salts are filtered off
  4. washby rinsing with acetone
  5. distillationThe solvent and the excess 1,6-dibromohexan are distilled off in vacuo
  6. customthe residue is purified by means of column chromatography (silica gel, chloroform/petroleum ether 1:2)

Sources & evidence

ORD record
ord-039c9a4e76a94de0897b89214f8d310b
Source dataset
uspto-grants-2009_02
Patent number
US07485742B2

Reaction notes

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