Oxygen → HCID 53918584, compound

HRID 1413229Notes

Reaction equation

HRID 1413229 reaction equation
[O:1]=O.[C:3]([O:6][CH:7]([CH:12]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=[CH:13]1)C(Cl)(Cl)Cl)(=O)C.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[Na]>CO.Cl>[CH:12]1([C:7]([O:6][CH3:3])=[O:1])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=[CH:13]1

Participants

7

Reactant 4

HCID 977OxygenHCID 212261,10-Phenanthroline hydrateHCID 5360545SodiumHCID 54311491HCID 54311491, compound

Product 1

HCID 53918584HCID 53918584, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

A stream of dry oxygen was passed through a stirred solution (heated at 30°-35° C.) of 1-(2-cyclododecen-1-yl)-2,2,2-trichloroethyl acetate (12 g; 35 m. moles) in methanol (10 ml) and a solution of cupric chloride dihydrate (0.19 g; 1.1 m. moles) and 1,10-phenanthroline hydrate (0.56 g; 2.85 m. moles) in methanol (45 ml) in which sodium (1.39 g; 6.0 m. moles) had been dissolved was added portionwise over a period of 225 minutes. The mixture was then diluted with dilute hydrochloric acid (100 ml), extracted with ether (3×50 ml) and the combined ether extracts were washed with aqueous sodium carbonate solution (50 ml) and water (50 ml). The dried (MgSO4) extract was evaporated and the crude product (4.7 g) distilled to give methyl 2-cyclododecene-1-carboxylate (3.9 g; 56%), b.p. 90°-110° C./0.1 mm. G.L.C. analysis indicated a purity of 85%.

Workup

  1. additionwas added portionwise over a period of 225 minutes
  2. extractionextracted with ether (3×50 ml)
  3. washthe combined ether extracts were washed with aqueous sodium carbonate solution (50 ml) and water (50 ml)
  4. dry with materialThe dried (MgSO4)
  5. extractionextract
  6. customwas evaporated
  7. distillationthe crude product (4.7 g) distilled

Sources & evidence

ORD record
ord-164a59f92a84459bbc2d5e57e0bcf45e
Source dataset
uspto-grants-1981_02
Patent number
US04249015

Reaction notes

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