Water → HCID 18627211, compound

HRID 249060Notes

Reaction equation

HRID 249060 reaction equation
[CH2:1]([CH:4]([CH2:9][CH2:10][CH3:11])[CH2:5][CH2:6][CH2:7]Br)[CH2:2][CH3:3].CC([O-])(C)C.[K+].O>C1C=CC=CC=1.CS(C)=O>[CH2:5]([CH:4]([CH2:9][CH2:10][CH3:11])[CH2:1][CH:2]=[CH2:3])[CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 962WaterHCID 197628661-Bromo-4-propylheptaneHCID 23665647Potassium tert-butoxide

Product 1

HCID 18627211HCID 18627211, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

To 100 g of 4-propylheptyl bromide in 400 ml of benzene was added 90 g of t-BuOK in 300 ml of DMSO. The temperature was kept below 50° C. during the addition. The mixture was stirred for 2 hrs and 600 ml of water was added. The organic phase was separated and the aqueous phase extracted with petroleumether (b.p. 40°-60°). The combined organic phases were washed with water and brine. After drying with Na2SO4 and evaporation the residue was distilled. Yield: 23.2 g (b.p. 56°-59° C. /75 Torr). 1H-NMR(CDCl3): δ0.9(6H,CH3), 1.2(9H,CH2,CH), 2.0(2H,CH2C=C), 4.8-5.1(2H,CH2 =C), 5.5-6.0(1H,CH=C)

Workup

  1. additionThe temperature was kept below 50° C. during the addition
  2. customThe organic phase was separated
  3. extractionthe aqueous phase extracted with petroleumether (b.p. 40°-60°)
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialAfter drying with Na2SO4 and evaporation the residue
  6. distillationwas distilled

Sources & evidence

ORD record
ord-258e1adfab3742ad88edbf307d025950
Source dataset
uspto-grants-1993_05
Patent number
US05212305

Reaction notes

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