1-Octanol → HCID 19743089, compound

HRID 2254670Notes

Reaction equation

HRID 2254670 reaction equation
[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(O)CCCCCCC.BrCCCC#[N:30].[OH-].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.O.C1C=CC=CC=1>[C:1](#[N:30])[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 9571-OctanolHCID 14798Sodium HydroxideHCID 214124-BromobutyronitrileHCID 19743090HCID 19743090, compound

Product 1

HCID 19743089HCID 19743089, compoundYield 16%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

5-Oxatridecanoic acid (O5, C13)--n-Octanol [CH3 (CH2)7OH, 8.0 g, 61.43 mmol] and 4-bromobutyronitrile [Br(CH2)3CN, 9.09 g, 61.43 mmol] were added to a solution of NaOH (50% aqueous, 50 mL), benzene (50 mL) and Bu4NHSO4 (2.61 g, 7.68 mmol). The mixture was stirred for 3 days at room temp. Water (50 mL) was added and then the mixture was extracted with ethyl acetate (4×60 mL), washed with water (2×40 mL) dried over Na2SO4 and distilled (Kugelrohr) to yield 5-oxatridecanonitrile (1.90 g, 16%) as a colorless oil that was used directly in the subsequent reaction.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (4×60 mL)
  2. washwashed with water (2×40 mL)
  3. dry with materialdried over Na2SO4
  4. distillationdistilled (Kugelrohr)

Sources & evidence

ORD record
ord-664e0d5b9a0e40e695ef39480b5f17a5
Source dataset
uspto-grants-1993_08
Patent number
US05236955

Reaction notes

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