Triethyl phosphite → HCID 54046773, compound

HRID 1284173Notes

Reaction equation

HRID 1284173 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].P(OCC)(OCC)OCC.C[O-].[Na+].[CH3:25][O:26][C:27]([CH3:37])([CH3:36])[CH2:28][CH2:29][CH2:30][CH:31]([CH3:35])[CH2:32][CH2:33]O>O.CN(C)C=O>[CH3:25][O:26][C:27]([CH3:36])([CH3:37])[CH2:28][CH2:29][CH2:30][CH:31]([CH3:35])[CH2:32][CH:33]=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 31215Triethyl phosphiteHCID 660114-Nitrobenzyl bromideHCID 1700411-Octanol, 7-methoxy-3,7-dimethyl-HCID 10942334Sodium Methoxide

Product 1

HCID 54046773HCID 54046773, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture consisting of 5.4 g (0.025 mol) of p-nitrobenzyl bromide and 4.15 g (0.025 mol) of triethyl phosphite is stirred at 90°, over the course of 1 hour and under nitrogen. The resulting ethyl bromide is distilled off from the reaction vessel. The obtained solution is then evacuated and stirred at a bath temperature of 110° for one further hour in a water jet vacuum. A suspension consisting of 1.68 g (0.030 mol) of sodium methylate and 10 cc of absolute dimethylformamide is carefully added at 0° to the residue. 4.65 g (0.025 mol) of 7-methoxy-3,7-dimethyloctanol in a small amount of dimethylformamide are subsequently added over the course of 5 minutes to the red reaction mixture which is stirred at 0° for 1 hour and at room temperature for 90 minutes. The ruby-coloured solution gradually turns dark brown. 60 cc of water are added and the reaction mixture is extracted with hexane. The extracts are washed with water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated at 40° /20 mm Hg. After chromatography of the residue on silica gel with hexane/ethyl acetate (97:3) and (94:6), pure 1-(8-methoxy-4,8-dimethyl-1-nonenyl)-4-nitrobenzene is obtained as a slightly yellow oil. nD20 = 1.5473

Workup

  1. distillationThe resulting ethyl bromide is distilled off from the reaction vessel
  2. customThe obtained solution is then evacuated
  3. stirringstirred at a bath temperature of 110° for one further hour in a water jet vacuum
  4. additionis carefully added at 0° to the residue
  5. stirringis stirred at 0° for 1 hour and at room temperature for 90 minutes
  6. extractionthe reaction mixture is extracted with hexane
  7. washThe extracts are washed with water and saturated sodium chloride solution
  8. dry with materialdried over magnesium sulphate
  9. customevaporated at 40° /20 mm Hg

Sources & evidence

ORD record
ord-ec721ebcb2cd402289704fafd5fb1b35
Source dataset
uspto-grants-1976_08
Patent number
US03978097

Reaction notes

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