Sulfuric Acid → HCID 53878153, compound

HRID 596646Notes

Reaction equation

HRID 596646 reaction equation
[Mg].[CH:2](Br)=[CH2:3].[CH3:5][C:6]([CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:7][CH2:8][CH2:9][C:10](=[O:13])[CH2:11][CH3:12].S(=O)(=O)(O)O>O1CCCC1>[CH2:11]([C:10]([OH:13])([CH2:9][CH2:8][CH:7]=[C:6]([CH3:5])[CH2:14][CH:15]([CH3:16])[CH3:17])[CH:2]=[CH2:3])[CH3:12]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 11641BromoetheneHCID 5462224MagnesiumHCID 54268130HCID 54268130, compound

Product 1

HCID 53878153HCID 53878153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a Grignard solution, prepared from 12.5 g. of magnesium and 57.8 g. of vinyl bromide in 130 ml. of tetrahydrofuran, is slowly added dropwise at 0°-5° C. a solution of 40.11 g. of 7,9-dimethyl-6-decen-3-one in 90 ml. of tetrahydrofuran. The mixture is left to stir for 2 hours at room temperature, then poured on to 300 ml. of ice-water, acidified with dilute sulphuric acid and extracted three times with ether. The extracts are washed with 10% by weight aqueous sodium bicarbonate solution and saturated sodium chloride solution, dried over sodium sulphate and evaporated. By distillation there is obtained pure 3-ethyl-7,9-dimethyl-1,6-decadien-3-ol; nD24 = 1.4631; boiling point - 71° C./0.65 mm Hg.

Workup

  1. customTo a Grignard solution, prepared from 12.5 g
  2. waitThe mixture is left
  3. additionpoured on to 300 ml
  4. extractionextracted three times with ether
  5. washThe extracts are washed with 10% by weight aqueous sodium bicarbonate solution and saturated sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. distillationBy distillation there

Sources & evidence

ORD record
ord-5318344fc1b14331b13712e0ae8503ef
Source dataset
uspto-grants-1977_03
Patent number
US04011335

Reaction notes

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