Diethylene Glycol → Ethanol, 2-[2-[(tetrahydro-2H-pyran-2-yl)oxy]ethoxy]-

HRID 2276825Notes

Reaction equation

HRID 2276825 reaction equation
[CH2:1]([OH:7])[CH2:2][O:3][CH2:4][CH2:5][OH:6].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(Cl)Cl>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:7][CH2:1][CH2:2][O:3][CH2:4][CH2:5][OH:6]

Participants

5

Reactant 3

HCID 8117Diethylene GlycolHCID 8894TetrahydropyranHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 558984Ethanol, 2-[2-[(tetrahydro-2H-pyran-2-yl)oxy]ethoxy]-Yield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 800 mL of CH2Cl2 were added diethylene glycol (57 mL, 0.6 mol) and p-toluenesulfonic acid monohydrate (5.7 g, 30 mmol) successively. Then tetrahydropyran (27.4 mL, 0.3 mol) was added dropwise at 0° C. The reaction mixture was stirred overnight and quenched with H2O, extracted with CH2Cl2, washed with H2O and brine successively, concentrated through rotary evaporation, and subjected to silica gel chromatography using CH2Cl2/MeOH as the eluent to afford compound 28 (32.5 g, 0.17 mol, 57% yield) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 4.59 (t, J=4.0 Hz, 1H), 3.85-3.80 (m, 2H), 3.68-3.64 (m, 4H), 3.59-3.55 (m, 3H), 3.48-3.44 (m, 1H), 2.98 (br, 1H), 1.81-1.76 (m, 1H), 1.71-1.65 (m, 1H), 1.59-1.46 (m, 4H).

Workup

  1. customquenched with H2O
  2. extractionextracted with CH2Cl2
  3. washwashed with H2O and brine successively
  4. concentrationconcentrated through rotary evaporation

Sources & evidence

ORD record
ord-7222c64e82ab460cade0a3f4f65a016c
Source dataset
uspto-grants-2015_09
Patent number
US09133114B2

Reaction notes

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