Reaction #833541

ord-4cc10e6f28fa4f5c80c958430a64fcea

Reaction equation

O=C(O)CCCCCCCCCCCCCCCO
16-hydroxyhexadecanoic acid
Br
HBr
→
O=C(O)CCCCCCCCCCCCCCCBr
desired product
Yield 99.0%
O=C(O)CCCCCCCCCCCCCCCBr
16-Bromohexadecanoic acid
Yield 99.0%

Reactants

O=C(O)CCCCCCCCCCCCCCCO
16-hydroxyhexadecanoic acid
Br
HBr

Reagents

None

Solvents

CC(=O)O
acetic acid

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Other16-Bromohexadecanoic acid was prepared
  2. 2
    TemperatureUpon cooling
  3. 3
    FiltrationIt was filtered out
  4. 4
    Washwashed with 3×100 ml of cold water
  5. 5
    OtherMaterial was purified by recrystallization from n-hexane
  6. 6
    Filtrationfiltered out
  7. 7
    Otherdried on high vacuum

Procedure

16-Bromohexadecanoic acid was prepared by refluxing for 48 hrs 5.0 gr (18.35 mmole) of 16-hydroxyhexadecanoic acid in 24 ml of 1:1 v/v mixture of HBr (48% aqueous solution) and glacial acetic acid. Upon cooling, crude product was solidified inside the reaction vessel. It was filtered out and washed with 3×100 ml of cold water. Material was purified by recrystallization from n-hexane, filtered out and dried on high vacuum. 6.1 gr (99% yield) of the desired product were obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07393645B2uspto-grants-2008_07