3,4-dihydro-2H-pyran → p-Tetrahydropyranyloxystyrene

HRID 327752

Reaction equation

HRID 327752 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.[OH-].[Na+]>C(OCC)C>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 14798Sodium HydroxideHCID 624534-VinylphenolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 9942467p-Tetrahydropyranyloxystyrene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 250 ml round-bottomed flask, 15 g (125 mmol) of 4-hydroxystyrene and 0.4 g (2.3 mmol) of p-toluenesulfonic acid monohydrate are dissolved in 120 ml of diethyl ether. Then, at 5° C., 11.6 g (137 mmol) of 3,4-dihydro-2H-pyran are added dropwise over a period of 10 minutes. The mixture is allowed to reach room temperature and is further stirred for 20 hours. 1N NaOH solution is then added and the organic phase is washed twice with water, dried over magnesium sulfate and concentrated to yield 23.3 g (114 mmol, 90% of the theoretical yield) of 4-tetrahydropyran-2-yloxystyrene in the form of a colourless oil that can be used for the copolymerisation without being further purified. 1H-NMR (CDCl3, 100 mHz): δ7.37/d (J=9 Hz)/2H, 7.02/d (J=9 Hz)/2H, 6.52/dd (J1 =18 Hz, J2 =11 Hz)/1H, 5.50/dd (J1 =18 Hz, J2 =2 Hz)/1H, 5.41/m/1H, 5.11/dd (J1 =11 Hz, J2 =2 Hz)/1H, 4.0-3.7/m/1H, 3.7-3.4/m/1H, 2.2-1.2/m/6H.

Workup

  1. customto reach room temperature
  2. washthe organic phase is washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto yield 23.3 g (114 mmol, 90% of the

Sources & evidence

ORD record
ord-75947710e9094a41bdbb2a3459e26f28
Source dataset
uspto-grants-1993_12
Patent number
US05274060

Linked notes

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