Ethyl chloroacetate → 2,6,10-Trimethyl-5,9-undecadienal (mixture of all stereo forms)

HRID 1578809Notes

Reaction equation

HRID 1578809 reaction equation
[CH2:1]([CH2:11]C(=O)C)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].ClCC([O:19][CH2:20][CH3:21])=O.[O-][CH2:23]C.[Na+].[OH-].[K+]>CO.C(O)(=O)C.O>[CH3:23][CH:21]([CH2:11][CH2:1][CH:2]=[C:3]([CH3:4])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])[CH:20]=[O:19]

Participants

8

Reactant 4

HCID 7751Ethyl chloroacetateHCID 14797Potassium HydroxideHCID 1549778GeranylacetoneHCID 2723922Sodium ethoxide

Product 1

HCID 911152,6,10-Trimethyl-5,9-undecadienal (mixture of all stereo forms)Yield 73.6%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a mixture of geranylacetone (171 g) and ethyl monochloroacetate (141 g) at -10°C in the nitrogen stream, sodium ethoxide (71 g) is portionwise added, and the resultant mixture is stirred for 6 hours. A solution of potassium hydroxide (99 g) in methanol (560 ml) is added thereto, and stirring is continued for 2 hours. The reaction mixture is poured into water and skaken with petroleum ether. The water layer is neutralized with acetic acid and extracted with ether. The ether extract is washed with water and dried. After evaporation of the ether, the residual material is distilled under reduced pressure to give 2,6,10-trimethyl-5,9-undecadienal (135 g) as a pale yellow oil. B.P. 100° to 103°C/0.4 mm Hg. Yield, 73.6%. IR: 2680, 1720 cm-1 (CHO).

Workup

  1. additionis portionwise added
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed with water
  5. customdried
  6. customAfter evaporation of the ether
  7. distillationthe residual material is distilled under reduced pressure

Sources & evidence

ORD record
ord-6345e99ee7ec4564936dd8c683feea50
Source dataset
uspto-grants-1976_02
Patent number
US03939202

Reaction notes

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