Glycol monoethyl ether → HCID 15020138, compound

HRID 1090940Notes

Reaction equation

HRID 1090940 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[CH2:14]([O:16][CH2:17][CH2:18][OH:19])[CH3:15]>>[C:11]([OH:13])(=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][O:19][CH2:18][CH2:17][O:16][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 8076Glycol monoethyl etherHCID 24758Sodium hydrideHCID 5482758-Bromooctanoic acid

Product 1

HCID 15020138HCID 15020138, compoundYield 8%

Procedure

NaH (2.4 g, 0.05 mol) was allowed to react with 2-ethoxyethanol (50 mL) during 30 min. 8-Bromooctanoic acid (4.8 g, 0.021 mol) was added, the solution heated at reflux for 24 h, cooled, and the solvent removed in vacuo. The residue was dissolved in ether, washed with water, the aqueous phase acidified (pH 1, HCl), and washed again with ether. The organic phase was dried (MgSO4), the solvent removed in vacuo, and the residue chromatographed (silica gel, 10%-25% Et2O/CH2Cl2), and distilled (Kugelrohr) to afford the title compound (0.4 g, 8%) as a yellow oil (bp 232° C./0.02 torr). IR: 1750 cm-1 : 1H NMR: 1.3 (t, 3H); 1.35 (bs, 6H); 1.6 (m, 4H); 3.5 (m, 8H). Anal. Calcd for C12H24O4 : C, 62.07; H, 10.41%. Found: C, 61.95; H, 10.46%.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 24 h
  3. temperaturecooled
  4. customthe solvent removed in vacuo
  5. dissolutionThe residue was dissolved in ether
  6. washwashed with water
  7. washwashed again with ether
  8. dry with materialThe organic phase was dried (MgSO4)
  9. customthe solvent removed in vacuo
  10. customthe residue chromatographed (silica gel, 10%-25% Et2O/CH2Cl2)
  11. distillationdistilled (Kugelrohr)

Sources & evidence

ORD record
ord-10ab6a57aafb4925b485be734c1c61d0
Source dataset
uspto-grants-1992_01
Patent number
US05082967

Reaction notes

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