Hydrochloric Acid → 4-(2-Hydroxyethyl)cyclohexan-1-one

HRID 1524757Notes

Reaction equation

HRID 1524757 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][OH:13])[CH2:7][CH2:6]2)OCC1.C1COCC1.Cl.C([O-])(O)=O.[Na+]>CC(C)=O>[OH:13][CH2:12][CH2:11][CH:8]1[CH2:9][CH2:10][C:5](=[O:1])[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 118054582-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-ol

Product 1

HCID 157003924-(2-Hydroxyethyl)cyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

2-(1,4-Dioxaspiro[4.5]dec-8-yl)ethanol (2.70 g, 0.0145 mol) was dissolved in acetone (10.00 mL) and THF (10.00 mL) and 6.00 M HCl (6.00 mL) was added. The reaction was stirred at 25° C. for 16 hours, neutralized with NaHCO3 solution and was then extracted with ethyl acetate. The organic extracts were washed with water, and with saturated NaCl, then dried (MgSO4) and concentrated in vacuo. The crude product was used in the next reaction without further purification. 1H NMR (CDCl3): 3.75 (m, 2H), 2.36 (m, 4H), 1.20-2.13 (m, 7H).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic extracts were washed with water
  3. dry with materialwith saturated NaCl, then dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was used in the next reaction without further purification

Sources & evidence

ORD record
ord-70939652667040928ee44ac5f007f5e2
Source dataset
uspto-grants-2015_07
Patent number
US09079912B2

Reaction notes

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