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

HRID 40981

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

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

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

Sources & evidence

ORD record: ord-febdcda125884427ad891da3ebe58e0e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530485B2

Linked notes

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