Reaction equation
C([CH:4]1[CH2:7][CH:6]([CH2:8][CH3:9])[CH2:5]1)(=O)C.ClC1C=CC=[C:13]([C:17]([O:19]O)=[O:18])C=1>C(Cl)(Cl)Cl>[C:17]([O:19][CH:4]1[CH2:5][CH:6]([CH2:8][CH3:9])[CH2:7]1)(=[O:18])[CH3:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5.5 g of the 1-acetyl-3-ethylcyclobutane, and 10.7 g of m-chloroperbenzoic acid in 107 ml chloroform was allowed to stand for five days in the dark. The reaction mixture was cooled via external ice cooling and filtered. The filtrate was diluted with CHCl3 and washed with 10 percent aqueous sodium thiosulfate, 10 percent aqueous sodium carbonate and brine, dried over Na2SO4, and filtered. The solution was subjected to distillation (aspirator vacuum) to afford 3.55 g of 1-acetoxy-3-ethylcyclobutane, as a clear oil (bp 65°-67°). The material had the following spectral chracteristics: nmr (CDCl3) δ 0.82 (3H, t, J=7.0 Hz) 1.10 and 1.12, (same side product noted in the 1-acetyl compound spectra), 1.0-2.5 l (7H, m), 2.01 (3H, s) and 4.9 (1H, m); ir (CHCl3) 950, 1040, 1085, 1205, 1250, 1375, 1460, 1720, 2870, 2925 and 2960 cm-1 along with trace of 3200-3600 (broad) and 3600 cm-1 for the same side product noted in the 1-acetyl the compound spectra.
Workup
- temperatureThe reaction mixture was cooled via external ice cooling
- filtrationfiltered
- additionThe filtrate was diluted with CHCl3
- washwashed with 10 percent aqueous sodium thiosulfate, 10 percent aqueous sodium carbonate and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- distillationThe solution was subjected to distillation (aspirator vacuum)
Sources & evidence
- ORD record
- ord-a7fe7333e7554d7486e0f069b4b08984
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04275224
Linked notes
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