Benzene → HCID 53911644, compound

HRID 436299Notes

Reaction equation

HRID 436299 reaction equation
[CH3:1][C:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:3][C:4]([OH:6])=[O:5].C(Cl)(=O)C(Cl)=O.[CH:24]1[CH:29]=[CH:28][CH:27]=CC=1>>[CH3:1][C:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:17])[CH2:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:3][C:4]([O:6][CH2:27][CH:28]1[CH2:24][CH2:29]1)=[O:5]

Participants

4

Reactant 3

HCID 241BenzeneHCID 65578Oxalyl chlorideHCID 53923510HCID 53923510, compound

Product 1

HCID 53911644HCID 53911644, compound

Procedure

To 1.56 g. of 3,7,11-trimethyldodec-2-enoic acid, under nitrogen, is added dry benzene and oxalyl chloride (2.4 g.). The mixture is stirred 2 hours and then concentrated in vacuo. To the concentrate is added fresh dry benzene and 1.6 g. of cyclopropylmethyl alcohol and the mixture stirred overnight at room temperature. The reaction is worked up by pouring into water and extracting with ether. The organic phase is washed with brine, stirred over neutral alumina (Act. III), concentrated under reduced pressure and purified by distillation to yield cyclopropylmethyl 3,7,11-trimethyldodec-2-enoate, b.p. 90° (bath) at 0.005 mm.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the concentrate is added fresh dry benzene and 1.6 g
  3. stirringof cyclopropylmethyl alcohol and the mixture stirred overnight at room temperature
  4. additionby pouring into water
  5. extractionextracting with ether
  6. washThe organic phase is washed with brine
  7. stirringstirred over neutral alumina (Act. III)
  8. concentrationconcentrated under reduced pressure
  9. distillationpurified by distillation

Sources & evidence

ORD record
ord-e90c495deeef4bf182af11ca05eb4039
Source dataset
uspto-grants-1977_02
Patent number
US04008258

Reaction notes

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