Water → HCID 14789683, compound

HRID 1090943Notes

Reaction equation

HRID 1090943 reaction equation
[OH2:1].[CH2:2]([OH:16])[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH3:15]>OS(O)(=O)=O.CC(O)=O>[C:2]([OH:1])(=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 962Water2×HCID 14789682HCID 14789682, compound

Product 1

HCID 14789683HCID 14789683, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

Kiliani reagent [Chem. Ber. 34, 3562 (1901)] was prepared in situ by dissolving Na2Cr2O7 2H2O (3 g) in a cold solution of H2SO4 (4 g) and water (13.5 g). To a solution of compound 6 (1.2 g, 5.5 mmol) in AcOH (28 mL) was added Kiliani reagent (20 g) at 0° C. The reaction mixture was stirred for 7 h at room temperature. Water (120 mL) was added to the mixture and then extracted with EtOAc (2×100 mL). The organic phase was washed with water (2×30 mL) and dried (Na2SO4). The residual oil was purified by column chromatography on silica gel with CHCl3 :MeOH (7:1) and subsequent Kugelrohr distillation to give the title product (1) (0.7 g, 52%); bp 128° C.-132 ° C./0.1 torr); IR(neat): 3000 (broad) and 1730 cm-1 ; 1H NMR: 1.23 (t, 3H, J=7.4 Hz), 1.3-1.8 (m, 10H), 2.38 (t, 2H, J=5.4 Hz), 3.3-3.6 (m 8H), and 9.98 ppm (b s, lH); Anal. Calcd for C12H24O4 : C, 62.04; H, 10.41%. Found: C, 61.95; H, 10.43%.

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. washThe organic phase was washed with water (2×30 mL)
  3. dry with materialdried (Na2SO4)
  4. distillationThe residual oil was purified by column chromatography on silica gel with CHCl3 :MeOH (7:1) and subsequent Kugelrohr distillation

Sources & evidence

ORD record
ord-f96a793eaf8247a3b254d085de50ffdf
Source dataset
uspto-grants-1992_01
Patent number
US05082967

Reaction notes

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