Isopropanol → Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate

HRID 1787398Notes

Reaction equation

HRID 1787398 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[C:6]1[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)[CH3:2].C(O)(C)C>[Pd].C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]1[CH2:15][CH2:14][C:9]2([O:10][CH2:11][CH2:12][O:13]2)[CH2:8][CH2:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 373318Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl ester

Product 1

HCID 15700391Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetateYield 94.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Second Step: 267.3 g of the compound (11), 5.0 g of Pd/C, 500 mL of isopropyl alcohol (IPA) and 500 mL of toluene were added to a reactor, and stirred under hydrogen atmosphere for 24 hours. After confirming that the reaction had been completed by GC analysis, the Pd/C was filtered off, and the solvent was removed by distillation under reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using heptane as eluent, and the solvent was distilled off under reduced pressure to obtain 255.2 g of (1,4-dioxaspiro[4,5]dec-8-yl)acetic acid ethyl ester (12) as a colorless liquid.

Workup

  1. filtrationthe Pd/C was filtered off
  2. customthe solvent was removed by distillation under reduced pressure
  3. customto obtain a residue
  4. customThe resulting residue was purified by silica gel column chromatography
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cf277ac2859a4c17bd2edeb5e6c4525f
Source dataset
uspto-grants-2009_03
Patent number
US07510749B2

Reaction notes

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