Stearoyl chloride → HCID 70359046, compound

HRID 745715Notes

Reaction equation

HRID 745715 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH:6]([OH:15])[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(Cl)(=O)CCCCCCCCCCCCCCCCC.C1(C(C(C2C=CC=CC=2)O)=O)C=CC=CC=1.C(S([O-])(=O)=O)CCCCCCCCCCCCCCC.F[C:76](F)([C:80](F)(F)[C:81](F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)[C:77]([O-:79])=[O:78]>C(N(CC)CC)C.C1(C)C=CC=CC=1>[C:77]([OH:79])(=[O:78])[CH2:76][CH2:80][CH2:81][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:8][CH2:7][CH2:6][CH2:5][CH2:16][CH2:17][CH2:18][CH2:3][CH3:4].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][CH:18]=1)[CH:6]([OH:15])[C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 8212Stearoyl chlorideHCID 8400BenzoinHCID 4622696HCID 4622696, compound2×HCID 4986139Perfluorooctanoate2×HCID 9991962HCID 9991962, compound

Product 1

HCID 70359046HCID 70359046, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Procedure

3'-Methoxybenzoin (5 g, 0.021 mol) was dissolved in 200 ml of toluene containing one equivalent of triethylamine. One equivalent of octadecanoyl chloride in 20 ml of toluene was added slowly to the cooled (ice bath) stirred benzoin solution. Stirring was continued with ice bath cooling for one hour. The reaction mixture was then filtered free of precipitated amine salt and the filtrate was evaporated to give an oil which solidified to give a low melting solid. The hexadecanesulfonate (Compound 14) and perfluorooctanoate (Compound 15) (m.p. 55°-58° C.) esters were similarly prepared from the corresponding acid chlorides.

Workup

  1. temperaturecooled (ice bath)
  2. customwas continued with ice bath
  3. temperaturecooling for one hour
  4. filtrationThe reaction mixture was then filtered free of precipitated amine salt
  5. customthe filtrate was evaporated
  6. customto give an oil which
  7. customto give a low melting solid

Sources & evidence

ORD record
ord-416b98a08c984043b5c0db4327ba5941
Source dataset
uspto-grants-1986_07
Patent number
US04599273

Reaction notes

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