Ethyl vinyl ether → HCID 89704532, compound

HRID 716481Notes

Reaction equation

HRID 716481 reaction equation
[CH:1]1([OH:13])[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH:26]([O:28][CH2:29][CH3:30])=[CH2:27]>CC(OC)(C)C>[CH2:26]([O:28][CH:29]([O:13][CH:1]1[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1)[CH3:30])[CH3:27]

Participants

5

Reactant 3

HCID 8023Ethyl vinyl etherHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 70475755HCID 70475755, compound

Product 1

HCID 89704532HCID 89704532, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Conditions

Temperature
40 °C

Procedure

To a mechanically stirred mixture of E,E-4,8-cyclododecadien-1-ol (99% (E,E)/1% (E/Z), 2.0 g, 11 mmol), toluene sulphonic acid monohydrate (0.15 g, 2 mmol) and MTBE (methyl terbutyl ether, 20 mL) was added drop wise ethyl vinyl ether (5 g) over 15 minutes. The reaction mixture was heated at reflux at 40° C. for 1 hour, then diluted with MTBE, washed with aqueous NaHCO3, water and brine. The solvent was evaporated and the product (4.5 g) purified by flash distillation (Kugelrohr, 86° C., 0.1 mbar) and liquid chromatography (silica gel 100 g; eluent=heptane/ethyl acetate 95/5).

Workup

  1. temperatureThe reaction mixture was heated
  2. washwashed with aqueous NaHCO3, water and brine
  3. customThe solvent was evaporated
  4. distillationthe product (4.5 g) purified by flash distillation (Kugelrohr, 86° C., 0.1 mbar) and liquid chromatography (silica gel 100 g; eluent=heptane/ethyl acetate 95/5)

Sources & evidence

ORD record
ord-a58c58168c444700841388caf485e349
Source dataset
uspto-grants-2015_11
Patent number
US09187710B2

Reaction notes

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