Hydrochloric Acid → HCID 23393477, compound

HRID 498142Notes

Reaction equation

HRID 498142 reaction equation
Cl.[C:2]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)OCC[O:16]1)(=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>O1CCCC1>[C:2]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](=[O:16])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)(=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22320894HCID 22320894, compound

Product 1

HCID 23393477HCID 23393477, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

2.32 ml of a 1N solution of HCl were added to a solution of 4.37 g (13.0 mmol) of 4-(2-phenyl-1,3-dioxolan-2-yl)butyl heptanoate obtained under d) in 18 ml of THF (tetrahydrofuran). The reaction mixture was heated to 40° C. for 24 h, cooled down to room temperature, extracted with ethyl acetate (2×) and washed with a sat. solution of NaCl (3×). The organic phase was dried (Na2SO4) and concentrated. Column chromatography (SiO2, heptane/ether 8:2) afforded 2.74 g (73%) of a colourless oil, which crystallises at 4° C.

Workup

  1. temperaturecooled down to room temperature
  2. extractionextracted with ethyl acetate (2×)
  3. washwashed with a sat. solution of NaCl (3×)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40067c330f1f4c39b0cd428c540b407b
Source dataset
uspto-grants-2005_09
Patent number
US06949680B2

Reaction notes

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