Trifluoroacetic acid → (3RS)-3-acetoxytetradecanoic acid

HRID 2164400Notes

Reaction equation

HRID 2164400 reaction equation
FC(F)(F)C(O)=O.[C:8]([O:11][CH:12]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])(=[O:10])[CH3:9]>C1C=CC=CC=1.C1(C)C=CC=CC=1>[C:8]([O:11][CH:12]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:13][C:14]([OH:16])=[O:15])(=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21769584Tert-butyl 3-(acetyloxy)tetradecanoate

Product 1

HCID 14803886(3RS)-3-acetoxytetradecanoic acidYield 85.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

Trifluoroacetic acid (32 ml) was added to t-butyl (3RS)-3-acetoxytetradecanoate (14 g) under ice-cooling. The mixture was stirred at the same temperature for 2 hours. The mixture was concentrated under reduced pressure to give a residue. The residue was dissolved in a mixture of benzene and toluene, and concentrated under reduced pressure to give (3RS)-3-acetoxytetradecanoic acid (10.0 g).

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give a residue
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ecd8ab22436f4b6c8b0c4c85309815fc
Source dataset
uspto-grants-1985_03
Patent number
US04504472

Reaction notes

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