Acetonitrile → HCID 14988633, compound

HRID 728345Notes

Reaction equation

HRID 728345 reaction equation
[CH3:1]/[C:2](/[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:17])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:3]/[C:4]([OH:6])=O.C(#N)C.C(OP(Cl)(=O)OCC)C.[NH2:30][C:31]1[CH:36]=[C:35]([CH3:37])[C:34]([OH:38])=[C:33]([CH3:39])[CH:32]=1>C(N(CC)CC)C>[CH3:1]/[C:2](/[CH2:7][CH2:8]/[CH:9]=[C:10](\[CH3:17])/[CH2:11][CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:3]/[C:4]([NH:30][C:31]1[CH:36]=[C:35]([CH3:37])[C:34]([OH:38])=[C:33]([CH3:39])[CH:32]=1)=[O:6]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 13139Diethyl chlorophosphateHCID 826684-Amino-2,6-dimethylphenolHCID 15559241HCID 15559241, compound

Product 1

HCID 14988633HCID 14988633, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Under ice-cooling, to a solution of 0.9 g of 3,7,11-trimethyl-(2Z,6E)-2,6,10-dodecatrienoic acid in 10 m of acetonitrile are added 578 mg of triethylamine, then 854 mg of diethylphosphorochloridate. After the mixture is stirred for 30 minutes, 522 mg of 4-amino-2,6-dimethylphenol is added and the reaction mixture is stirred at room temperature. Ice chips are added into the reaction mixture, the mixture is extracted with isopropyl ether and the extracted with 10% hydrochloric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride, followed by drying and then evaporation of the solvent. The residue is purified by silica gel column chromatography [solvent: ethyl acetate-hexane (1:3)] to give 580 mg of 4-[3,7,11-trimethyl-(2Z,6E)-2,6,10-dodecatrienoylamino]-2,6-dimethylphenol

Workup

  1. stirringthe reaction mixture is stirred at room temperature
  2. additionIce chips are added into the reaction mixture
  3. extractionthe mixture is extracted with isopropyl ether
  4. extractionthe extracted with 10% hydrochloric acid, water, 5% aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride
  5. customby drying
  6. customevaporation of the solvent
  7. customThe residue is purified by silica gel column chromatography [solvent: ethyl acetate-hexane (1:3)]

Sources & evidence

ORD record
ord-087aa510b41c44c1aab75a7f40f26db9
Source dataset
uspto-grants-1991_09
Patent number
US05047555

Reaction notes

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