3,4-dihydro-2H-pyran → 6-(Tetrahydro-2H-pyran-2-yloxy)-1-hexanol

HRID 1581106Notes

Reaction equation

HRID 1581106 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13]>C(Cl)(Cl)Cl.Cl>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][OH:14]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 123741,6-Hexanediol

Product 1

HCID 5589936-(Tetrahydro-2H-pyran-2-yloxy)-1-hexanolYield 57%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6212ChloroformSolvent

Procedure

6-(2-Tetrahydropyranyloxy)hexanol was prepared by a modification of the method described by Bohlmann, Jeute and Reinecke, Chem. Ber., 1969, 102, 3283. 3,4-Dihydro-2-H-pyran (33.6 g., 0.4 mole) was added dropwise at 30°C. with stirring to hexane-1,6-diol (47.2 g., 0.4 mole) in chloroform (500 ml.) and concentrated hydrochloric acid (30 drops). The temperature was allowed to rise to 40°C. and maintained at this level for 3 hours. The solution was then washed with aqueous sodium bicarbonate and then water and dried over potassium carbonate. The solvent was removed in vacuo, and the residue distilled under reduced pressure to give 6-(2-tetrahydropyranyloxy)hexanol (46.1 g., 57%), b.p. 102°-120°C./0.2 mm.Hg.

Workup

  1. custom6-(2-Tetrahydropyranyloxy)hexanol was prepared by a modification of the method
  2. customto rise to 40°C.
  3. temperaturemaintained at this level for 3 hours
  4. washThe solution was then washed with aqueous sodium bicarbonate
  5. dry with materialwater and dried over potassium carbonate
  6. customThe solvent was removed in vacuo
  7. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-16b4ed5f480544808dd4e4223bd4e112
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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