1-Dodecanol → HCID 54297401, compound

HRID 2081936Notes

Reaction equation

HRID 2081936 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].S(Cl)(Cl)=O.[N+](C1C=CC=CC=1C(Cl)=O)([O-])=O.[CH2:29](O)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>C(OCC)(=O)C.N1C=CC=CC=1.C(#N)C.CN(C)C=O>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH3:29])=[O:7])([O-:3])=[O:2]

Participants

9

Reactant 4

HCID 81931-DodecanolHCID 110872-Nitrobenzoic acidHCID 118752-Nitrobenzoyl chloride2×HCID 24386Thionyl Chloride

Product 1

HCID 54297401HCID 54297401, compoundYield 89.9%

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 83.5 g of o-nitrobenzoic acid, 1 ml of dimethylformamide and 100 ml of thionyl chloride was heated under reflux for 3 hours. The resulting reaction mixture was concentrated under reduced pressure with an aspirator to yield yellow, oily o-nitrobenzoyl chloride. The thus obtained o-nitrobenzoyl chloride was added dropwise to 300 ml of acetonitrile, in which 88.4 g of n-dodecanol and 41 ml of pyridine were dissolved, at room temperature with stirring over a period of 30 minutes. After one hour's stirring, the resulting solution was mixed with 600 ml of ethyl acetate, and washed three times with 500 ml of water being used for each wash, to extract the product with the ethyl acetate. The ethyl acetate solution was dried over sodium sulfate, and then concentrated to give 143 g of light yellow oily dodecyl o-nitrobenzoate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. customThe resulting reaction mixture
  4. concentrationwas concentrated under reduced pressure with an aspirator
  5. customto yield yellow
  6. dissolutionwere dissolved, at room temperature
  7. stirringAfter one hour's stirring
  8. washwashed three times with 500 ml of water being
  9. extractionto extract the product with the ethyl acetate
  10. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-bc4503f846bd443f8e956056338a228d
Source dataset
uspto-grants-1993_02
Patent number
US05187055

Reaction notes

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