Methanol → HCID 14986704, compound

HRID 465604Notes

Reaction equation

HRID 465604 reaction equation
CO.C[O:4][C:5]([CH:7]([CH2:13][CH:14]=[CH2:15])[CH2:8][CH2:9][CH2:10][C:11]#[N:12])=O.[BH4-].[Na+].COCCOC>O>[OH:4][CH2:5][CH:7]([CH2:13][CH:14]=[CH2:15])[CH2:8][CH2:9][CH2:10][C:11]#[N:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 80711,2-DimethoxyethaneHCID 4311764Sodium borohydrideHCID 149867035-Carbomethoxy-oct-7-enenitrile

Product 1

HCID 14986704HCID 14986704, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanol (4136 ml) is added dropwise over about 3 h to a mixture of 2054 g of 5-methoxycarbonyl-oct-7-enenitrile, 1286 g of sodium borohydride and 20.5 l of 1,2-dimethoxyethane heated at 75°. The reaction mixture is heated at 95° for 3.5 h, stirred at room temperature overnight, and cooled to 8° in an ice bath. Water (21.0 l) is added slowly, the mixture is again stirred for 1.5 h at room temperature, and then extracted with ethyl acetate (2×20 l). The combined extract is washed with brine, dried over sodium sulfate and evaporated to dryness at 65°-70°/3 mm Hg (=4.00 mbar). The residue is distilled to yield 6-hydroxy-5-(2-propenyl)-hexanenitrile, b.p. 113°-116°/0.8 mm Hg (=1.07 mbar).

Workup

  1. temperatureheated at 75°
  2. temperatureThe reaction mixture is heated at 95° for 3.5 h
  3. temperaturecooled to 8° in an ice bath
  4. stirringthe mixture is again stirred for 1.5 h at room temperature
  5. extractionextracted with ethyl acetate (2×20 l)
  6. extractionThe combined extract
  7. washis washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated to dryness at 65°-70°/3 mm Hg (=4.00 mbar)
  10. distillationThe residue is distilled

Sources & evidence

ORD record
ord-2837628f7b6c448c9392d30ec0b898dc
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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