Acetic Acid → HCID 18687295, compound

HRID 1872803Notes

Reaction equation

HRID 1872803 reaction equation
[CH:1](=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(O)(=O)C.[C-:20]#[N:21].[K+]>C(OCC)C>[OH:15][CH:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:20]#[N:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 31291Tetradecanal

Product 1

HCID 18687295HCID 18687295, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cooled solution of tetradecanal (18.75 g) in diethyl ether (100 ml) was added acetic acid (5.66 ml) and potassium cyanide (6.64 g). The mixture was warmed to room temperature and stirred for 72 hours. The resulting solution was washed with water, and the aqueous phase was extracted with diethyl ether (50 ml). The combined organic phase was dried, and concentrated to dryness. The residue was purified by silica gel chromatography and triturated in diisopropyl ether (10 ml) to give 2-hydroxypentadecanenitrile (4.66 g).

Workup

  1. washThe resulting solution was washed with water
  2. extractionthe aqueous phase was extracted with diethyl ether (50 ml)
  3. customThe combined organic phase was dried
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by silica gel chromatography
  6. customtriturated in diisopropyl ether (10 ml)

Sources & evidence

ORD record
ord-8d89f4c065a842e4b49363b51e5c7207
Source dataset
uspto-grants-2000_08
Patent number
US06110933

Reaction notes

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