Tetrahydrofuran → HCID 20492916, compound

HRID 434546Notes

Reaction equation

HRID 434546 reaction equation
O1CCCC1.[H-].[Na+].Cl[CH2:9][C:10]([CH3:12])=[CH2:11].[CH2:13]([O:15][CH2:16][CH2:17][OH:18])[CH3:14]>O.C(O)C>[CH2:9]([O:18][CH2:17][CH2:16][O:15][CH2:13][CH3:14])[C:10](=[CH2:11])[CH3:12]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8076Glycol monoethyl etherHCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydride2×

Product 1

HCID 20492916HCID 20492916, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Into a 22 liter flask equipped with a reflux condenser, mechanical stirrer, addition funnel and nitrogen gas inlet, was placed 12.5 liters of dry tetrahydrofuran and 1958 grams of a 60% oil dispersion of sodium hydride. The mixture was stirred and heated to a gentle reflux, then 2.99 Kg of 3-chloro-2-methyl propene was added as one portion. Next, 2.79 Kg of 2-ethoxyethanol was added dropwise during 3.5 hours with no external heating of the resulting exothermic reaction. Refluxing was continued for two additional hours, then the solution was cooled to room temperature. Excess sodium hydride was decomposed by carefully adding ethanol then enough water to dissolve the resulting salts. The organic layer was separated and distilled through a vigreaux column at 156°-158° C. The yield of product was 3490 grams and was 99.4% pure by G.L.P.C. analysis.

Workup

  1. customInto a 22 liter flask equipped with a reflux condenser, mechanical stirrer, addition funnel and nitrogen gas inlet
  2. temperatureheated to a gentle reflux
  3. temperatureno external heating of the resulting exothermic reaction
  4. temperatureRefluxing
  5. customThe organic layer was separated
  6. distillationdistilled through a vigreaux column at 156°-158° C

Sources & evidence

ORD record
ord-96e922937ad945dabb96267cd23e337e
Source dataset
uspto-grants-1983_08
Patent number
US04398001

Reaction notes

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