Ethylene Glycol → 1-(1,3-Dioxolane-2-yl)-3,3,3-trifluoropropane-2-one

HRID 869111Notes

Reaction equation

HRID 869111 reaction equation
[CH2:1]([O:3][CH:4]=[CH:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])[CH3:2].C(O)C[OH:14]>C1(C)C=CC=CC=1.O.CC1C=CC(S(O)(=O)=O)=CC=1>[O:3]1[CH2:1][CH2:2][O:14][CH:4]1[CH2:5][C:6](=[O:11])[C:7]([F:9])([F:10])[F:8]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 27803954-Ethoxy-1,1,1-trifluoro-3-buten-2-one

Product 1

HCID 552960491-(1,3-Dioxolane-2-yl)-3,3,3-trifluoropropane-2-oneYield 67.3%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

4-Methylbenzenesulfonic acid monohydrate (500.1 mg, 467.4 μL, 2.629 mmol) was added to a solution of 4-ethoxy-1,1,1-trifluoro-but-3-en-2-one (200.97 g, 1.195 mol) and ethylene glycol (77.27 g, 69.42 mL, 1.245 mol) in toluene (502.5 mL). The reaction mixture was heated to reflux for 90 min (oil bath). Then, the reflux was continued with simultaneous distillation of ethanol/toluene. The Dean-Stark was removed and the flask was connected to a distillation apparatus. 3-(1,3-Dioxolan-2-yl)-1,1,1-trifluoro-propan-2-one was distilled using a KNF pump (Bp 81° C.) as a light yellow oil (148 g, 67% yield). 1H NMR (500 MHz, CDCl3) δ 5.38-5.40 (t, 1H), 4.02-4.05 (m, 2H), 3.93-3.95 (m, 2H), 3.10 (d, 2H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 90 min (oil bath)
  3. distillationThen, the reflux was continued with simultaneous distillation of ethanol/toluene
  4. customThe Dean-Stark was removed
  5. distillation3-(1,3-Dioxolan-2-yl)-1,1,1-trifluoro-propan-2-one was distilled

Sources & evidence

ORD record
ord-443b33f208db4f75bbb860460b077ca0
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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