Hydrochloric Acid → heptadecane, 3-methyl-

HRID 2380171Notes

Reaction equation

HRID 2380171 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:3](=O)[CH3:4].O.NN.[OH-].[Na+].Cl>O.C(O)COCCO>[CH3:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 15376167HCID 15376167, compound

Product 1

HCID 94321heptadecane, 3-methyl-Yield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
200 °C

Procedure

2 g (7.46 mmol) of 3-methyl-heptadecan-2-one (Compound No. 3 of Table 1) are introduced into 10 ml of diethylene glycol, and the mixture is treated with 1.11 g (22.4 mmol) of hydrazine hydrate and 1.2 g (29.85 mmol) of sodium hydroxide. The mixture is stirred for twenty hours at 200° C. When the mixture has cooled to room temperature, it is treated with 100 ml of water, acidified with hydrochloric acid, with cooling, and extracted three times using cyclohexane. The combined organic extracts are washed twice with a little water, dried over sodium sulphate and concentrated. Separation by column chromatography using cyclohexane as the eluent gave 1.0 g (53% of theory) of 3-methylheptadecane.

Workup

  1. temperatureWhen the mixture has cooled to room temperature
  2. temperaturewith cooling
  3. extractionextracted three times
  4. washThe combined organic extracts are washed twice with a little water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customSeparation by column chromatography

Sources & evidence

ORD record
ord-8acf9980d905422eab83c4207ba7eae7
Source dataset
uspto-grants-1994_11
Patent number
US05365691

Reaction notes

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