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

HRID 2065475Notes

Reaction equation

HRID 2065475 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 1140TolueneSolvent2×

Conditions

Temperature
20 °C

Procedure

20.00 kg (182.50 mol) ethyl glycolate (A) were dissolved in 60.0 L toluene and 71.04 g (0.366 mol) 4-toluenesulphonic acid monohydrate were added. A solution of 15.83 kg (182.50 mol) 3,4-dihydro-2H-pyran in 40.0 L toluene was added dropwise at 20° C. to the reaction mixture obtained. Then the reaction mixture was stirred for 1 hour at 20° C. and after the reaction had ended 37.0 L water and 3.69 L (49.28 mol) ammonia solution (25%) were added. After phase separation the organic phase was washed with 40.0 L water and then the solvent was completely distilled off in vacuo.

Workup

  1. customobtained
  2. additionwere added
  3. customAfter phase separation the organic phase
  4. washwas washed with 40.0 L water
  5. distillationthe solvent was completely distilled off in vacuo

Sources & evidence

ORD record
ord-0b73801ab088438d9bfa9489d6ef3954
Source dataset
uspto-grants-2012_10
Patent number
US08288531B2

Reaction notes

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