Hydrochloric Acid → HCID 59030559, compound

HRID 1045366Notes

Reaction equation

HRID 1045366 reaction equation
[CH:1]1([C:4]2([OH:14])[CH2:13][CH2:12][C:7]3(OCC[O:8]3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.O.Cl>CC(C)=O.C(OCC)(=O)C>[CH:1]1([C:4]2([OH:14])[CH2:13][CH2:12][C:7](=[O:8])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59030604HCID 59030604, compound

Product 1

HCID 59030559HCID 59030559, compoundYield 35.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

8-Cyclopropyl-1,4-dioxaspiro[4.5]decan-8-ol (1.8 g) was dissolved in acetone (30 mL). A solution of water (15 mL) and conc. HCl was added. The reaction mixture was stirred overnight. The reaction mixture was taken in ethyl acetate and washed with sat. NaHCO3. Purification by silica chromatography produced 4-cyclopropyl-4-hydroxycyclohexanone (0.5 g, 27%). 1H NMR (400 MHz, CDCl3): δ 2.80-2.69 (m, 2H), 2.50-2.42 (m, 2H), 1.99-1.78 (m, 4H), 1.01-0.99 (m, 1H), 0.50-0.47 (m, 4H); MS (ESI) m/z: Calculated for C9H14O2: 154.1. found: 155.1 (M+H)+.

Workup

  1. washwashed with sat. NaHCO3
  2. customPurification by silica chromatography

Sources & evidence

ORD record
ord-a182d69a17e64c2299d39a420476a8e1
Source dataset
uspto-grants-2013_10
Patent number
US08569282B2

Reaction notes

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