3,4-dihydro-2H-pyran → 2-(4-(chloromethyl)benzyloxy)tetrahydro-2H-pyran

HRID 1417716Notes

Reaction equation

HRID 1417716 reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:8])=[CH:5][CH:4]=1.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1>ClCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:8])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 104902622-(4-(chloromethyl)benzyloxy)tetrahydro-2H-pyranYield 947.1%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

p-Hydroxymethylbenzyl chloride (1.33 kg, 1 mole) in dichloromethane (6 liters) was charged to a 10 liter Morton flask. Addition of 3,4-dihydro-2H-pyran (925 g, 1.1 moles) to the flask was followed by cooling to 5° C. Pyridinium p-toluenesulfonate (1.25 g, 5 mmoles) was added as a catalyst. The contents were allowed to warm up to 20°-25° C. and stirred for 24 hours. The contents were washed with water followed by a sodium bicarbonate solution and then dried over anhydrous magnesium sulfate. The residue, after removal of solvent, was kept under high vacuum (1-2 mm Hg) for 24 hours and provided 2.28 kg (95% yield) of the desired product. 1H NMR spectral data were as follows: (CDCl3, 300 MHz): δ 7.4 (s, 4H), 4.75 (t, 1H), 4.65 (AB quartet, 2H, J=13 Hz), 4.6 (s, 2H), 3.85 (m, 1H), 3.55 (m, 1H), 1.5-1.95 (m, 6H).

Workup

  1. temperatureto warm up to 20°-25° C.
  2. washThe contents were washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residue, after removal of solvent
  5. waitwas kept under high vacuum (1-2 mm Hg) for 24 hours

Sources & evidence

ORD record
ord-5e629364dadc49b2acb4e9eb02418d41
Source dataset
uspto-grants-1999_03
Patent number
US05877312

Reaction notes

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