Sodium Hydroxide → 2-Cyanomethyl-3-hexadecyloxypropanol

HRID 847014Notes

Reaction equation

HRID 847014 reaction equation
C([O:9][CH2:10][CH:11]([CH2:30][C:31]#[N:32])[CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])(=O)C1C=CC=CC=1.[OH-].[Na+]>CO.O1CCCC1>[C:31]([CH2:30][CH:11]([CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:10][OH:9])#[N:32]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 545411872-Cyanomethyl-3-hexadecyloxypropyl benzoate

Product 1

HCID 148349942-Cyanomethyl-3-hexadecyloxypropanolYield 67.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 12.42 g of 2-cyanomethyl-3-hexadecyloxypropyl benzoate n3' and 15.5 ml (31.0 mM) of 2N aqueous sodium hydroxide in 60 ml of methanol and 100 ml of tetrahydrofuran is stirred at room temperature for 1 hour and solvents are evaporated. The product is isolated by ethyl acetate extraction. The ethyl acetate layer is washed with water, dried over anhydrous magnesium sulfate and evaporated. Purification by column silica gel chromatography using n-hexane-ethyl acetate (4:1) affords 6.430 g (67.8% yield) of the titled compound Vn1.

Workup

  1. customsolvents are evaporated
  2. customThe product is isolated by ethyl acetate extraction
  3. washThe ethyl acetate layer is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customPurification by column silica gel chromatography

Sources & evidence

ORD record
ord-a2078c17ba76442db3253ee7fb39d8ea
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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