2-Butoxyethanol → HCID 15020137, compound

HRID 1090939Notes

Reaction equation

HRID 1090939 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[CH2:12]([O:16][CH2:17][CH2:18][OH:19])[CH2:13][CH2:14][CH3:15]>>[C:9]([OH:11])(=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][O:19][CH2:18][CH2:17][O:16][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 81332-ButoxyethanolHCID 202106-Bromohexanoic acidHCID 24758Sodium hydride

Product 1

HCID 15020137HCID 15020137, compoundYield 50%

Procedure

NaH (2.2 g, 0.045 mol) was allowed to react with 2-butoxyethanol (50 mL) during 1 h. 6-Bromohexanoic acid (4.2 g, 0.0215 mol) was added, the mixture was heated at reflux for 24 h, cooled, and the solvent was removed in vacuo. The residue was dissolved in ether (50 mL), washed with water (3×40 mL), the aqueous phase was acidified (pH 1.0, 6 M HCl), washed with ether, and the solvent removed in vacuo. The yellow oil was chromatographed (silica gel, 10%-30% Et2O/CH2Cl2) and distilled (Kugelrohr) to yield the title product (2.0 g, 50%, bp 120° C./0.02 torr). IR: 1740 cm-1. 1H NMR: 0.98 (t, 3H), 1.4 (m, 4H) 1.6 (m, 6H), 2.4 (t, 2H), 3.4 (t, 4H), 3.6 (s, 4H). Anal. Calcd for C12H24O4 : C, 62.04; H, 10.41%. Found C, 61.99; H, 10.47%

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 24 h
  3. temperaturecooled
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in ether (50 mL)
  6. washwashed with water (3×40 mL)
  7. washwashed with ether
  8. customthe solvent removed in vacuo
  9. customThe yellow oil was chromatographed (silica gel, 10%-30% Et2O/CH2Cl2)
  10. distillationdistilled (Kugelrohr)

Sources & evidence

ORD record
ord-8fa47a70da6240dcaa9ba308c72cefb7
Source dataset
uspto-grants-1992_01
Patent number
US05082967

Reaction notes

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