Oxalyl chloride → 9-Octadecene, 1-chloro-

HRID 544120Notes

Reaction equation

HRID 544120 reaction equation
[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(Cl)(=O)C([Cl:24])=O>C1(C)C=CC=CC=1>[CH2:1]([Cl:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 445639Oleic Acid

Product 1

HCID 53677849-Octadecene, 1-chloro-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a dry 4-neck-round bottomed flask equipped with nitrogen inlet, addition funnel, therometer, mechanical stirrer and heating means, under nitrogen, are cautiously (to avoid foaming), charged 229 g. of oleic acid (99% pure, m.p. 4°; b.p. 286°/100 mmHg), 263 ml of toluene and 109 ml. of oxalyl chloride (b.p. 63°-64°), at a rate so as to keep the (internal) reaction temperature between 25°-30°, over a period of about 15 minutes. After addition is complete the funnel is washed with an additional 25 ml. toluene. The reaction mixture is stirred 25°-30° for about one-half hour, and then at about 50°-55° for 1 hour. The toluene is then distilled off (initially at 35°-40°/63 mm vapor pressure; then at 30°-25°/26 mm for 1.5 hours) to obtain oleyl chloride, which is promptly used for the following Step B.

Workup

  1. customInto a dry 4-neck-round bottomed flask equipped with nitrogen inlet, addition funnel
  2. temperaturetherometer, mechanical stirrer and heating
  3. additioncharged 229 g
  4. customthe (internal) reaction temperature between 25°-30°
  5. additionAfter addition
  6. washis washed with an additional 25 ml
  7. waitat about 50°-55° for 1 hour
  8. distillationThe toluene is then distilled off (initially at 35°-40°/63 mm vapor pressure

Sources & evidence

ORD record
ord-29e49dd4f12b40b1803c115420286004
Source dataset
uspto-grants-1984_05
Patent number
US04448785

Reaction notes

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