Ammonia → ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate

HRID 2065476Notes

Reaction equation

HRID 2065476 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][OH:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.N>C1(C)C=CC=CC=1.O>[CH2:6]([O:5][C:1](=[O:4])[CH2:2][O:3][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][O:20]1)[CH3:7]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 80803,4-dihydro-2H-pyranHCID 12184Ethyl GlycolateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 10899396ethyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

100.00 kg (960.52 mol) ethyl glycolate (A) were dissolved in 180.0 L toluene and 365.22 g (1.92 mol) 4-toluenesulphonic acid monohydrate were added. At 20° C. a solution of 80.80 kg (960.52 mol) 3,4-dihydro-2H-pyran was added dropwise to the reaction mixture obtained and then the mixture was washed with 20.0 L toluene. The reaction mixture was stirred for 1 hour at 20° C. and after the reaction was complete it was combined with 100.0 L water and 6.53 kg (96.05 mol) ammonia solution (25%). After phase separation the organic phase was washed with 100.0 L water and then the solvent was distilled off completely in vacuo.

Workup

  1. customobtained
  2. washthe mixture was washed with 20.0 L toluene
  3. customAfter phase separation the organic phase
  4. washwas washed with 100.0 L water
  5. distillationthe solvent was distilled off completely in vacuo

Sources & evidence

ORD record
ord-60d547386d984488bc5c3ecadc9d0925
Source dataset
uspto-grants-2012_10
Patent number
US08288531B2

Reaction notes

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