Heptadecane, 1-chloro- → HCID 13109027, compound

HRID 864263Notes

Reaction equation

HRID 864263 reaction equation
[Na].C(Cl)C[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:20]([O:37]CCOCCOO)[CH2:21]CCCCCCCCCCCCCCC>C(O)COCCO>[CH2:13]([CH:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH3:4])[CH2:21][CH2:20][OH:37])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 43868Heptadecane, 1-chloro-HCID 5360545Sodium2×HCID 131719591HCID 131719591, compound

Product 1

HCID 13109027HCID 13109027, compound

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent2×

Conditions

Temperature
140 °C

Procedure

To a round bottom flask is added 42.4 (0.4 mol) of diethylene glycol under a nitrogen atmosphere. To this reaction mass is added 2.3 g (0.1 mole) of sodium over 1 hour. The reaction mass is heated to 130° C. whereby all of the sodium has reacted. Then 27.4 g (0.1 mol) of C17H35Cl is added over 1 hour and then kept for 17 hours at these conditions. Reaction temperature is then increased to 140° C. and kept for 17 hours at these conditions for 24 hours. The reaction mass upon cooling consists of 2 layers. GC shows the bottom layer to be mostly diethylene glycol. The reaction mass is filtered and the bottom diethylene glycol layer separated. The top organic layer is diluted with diethyl ether, water washed and dried over anhydrous MgSO4. After filtering, the organic layer is fractionally distilled to give a fraction at from 200°-220° C. and 2.25-2.5 mm containing the desired product, C17H35O(CH2CH2O)2OH, in two isomeric forms, one of which is the desired isomer of this invention, namely C8H17 (C6H13)CHCH2CH2 (OCH2CH2)2OH.

Workup

  1. customhas reacted
  2. customReaction temperature
  3. waitkept for 17 hours at these conditions for 24 hours
  4. temperatureThe reaction mass upon cooling
  5. filtrationThe reaction mass is filtered
  6. customthe bottom diethylene glycol layer separated
  7. additionThe top organic layer is diluted with diethyl ether, water
  8. washwashed
  9. dry with materialdried over anhydrous MgSO4
  10. filtrationAfter filtering
  11. distillationthe organic layer is fractionally distilled
  12. customto give a fraction at from 200°-220° C. and 2.25-2.5 mm

Sources & evidence

ORD record
ord-3b283c65998d4966ac93f4b38c0c2de8
Source dataset
uspto-grants-1996_10
Patent number
US05562866

Reaction notes

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