p-Toluenesulfonic acid → 2-[(4,4-Dimethyloct-1-YN-3-YL)oxy]oxane

HRID 1580299Notes

Reaction equation

HRID 1580299 reaction equation
[CH3:1][C:2]([CH3:11])([CH2:7][CH2:8][CH2:9][CH3:10])[CH:3]([OH:6])[C:4]#[CH:5].[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:6][CH:3]([C:2]([CH3:11])([CH3:1])[CH2:7][CH2:8][CH2:9][CH3:10])[C:4]#[CH:5]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8894TetrahydropyranHCID 145163694,4-Dimethyl-1-octyn-3-ol

Product 1

HCID 145163702-[(4,4-Dimethyloct-1-YN-3-YL)oxy]oxane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 58 parts of 4,4-dimethyl-1-octyn-3-ol in 116 parts by volume of dry benzene is added first 158 parts of tetrahydropyran then, with cooling, 0.29 part of p-toluenesulfonic acid. The reaction mixture is stored at room temperature for about 16 hours, then is diluted with benzene and washed successively with dilute aqueous sodium hydroxide and water. Drying over anhydrous sodium sulfate followed by removal of the solvent under reduced pressure affords 4,4-dimethyl-1-octyn-3-ol tetrahydropyran-2-yl ether.

Workup

  1. temperaturewith cooling
  2. washwashed successively with dilute aqueous sodium hydroxide and water
  3. dry with materialDrying over anhydrous sodium sulfate
  4. customfollowed by removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-64ed8ffe0f024fa89d9f374caddf8465
Source dataset
uspto-grants-1976_01
Patent number
US03932496

Reaction notes

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