3,4-dihydro-2H-pyran → 7-(2-Tetrahydropyranyloxy)heptanenitrile

HRID 372042Notes

Reaction equation

HRID 372042 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15]>Cl.C1C=CC=CC=1>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 873856-Cyano-1-hexanol

Product 1

HCID 205429327-(2-Tetrahydropyranyloxy)heptanenitrileYield 87.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 241BenzeneSolvent

Procedure

3,4-Dihydro-2H-pyran (272 g.) was added dropwise at 40° C. with stirring to a mixture of 7-hydroxyheptanenitrile (284 g.) and concentrated hydrochloric acid (10 drops). The temperature was allowed to rise to 65° C. and was maintained at this level for one hour. The solution was cooled and benzene (500 ml.) was added. The solution was washed with aqueous sodium bicarbonate and then water, and dried over sodium sulphate. The solvent was removed in vacuo, and the residue distilled under reduced pressure to give 7-(2-tetrahydropyranyloxy)heptanenitrile (411 g.), b.p. 100°-130° C./0.1 mm.Hg, nD25 1.455.

Workup

  1. customto rise to 65° C.
  2. temperaturewas maintained at this level for one hour
  3. temperatureThe solution was cooled
  4. washThe solution was washed with aqueous sodium bicarbonate
  5. dry with materialwater, and dried over sodium sulphate
  6. customThe solvent was removed in vacuo
  7. distillationthe residue distilled under reduced pressure

Sources & evidence

ORD record
ord-36f3dbdd8d184244a1f672997354f282
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

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