Hexadecanolide → 16-Iodohexadecanoic acid

HRID 1279134

Reaction equation

HRID 1279134 reaction equation
[C:1]1(=[O:18])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[IH:19].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[I:19][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:17])=[O:18]

Participants

5

Reactant 3

HCID 7984HexadecanolideHCID 24477Sodium ThiosulfateHCID 24841Hydrogen iodide

Product 1

HCID 4111116-Iodohexadecanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

16-Hexadecanolide (5.0 g, 0.02 mol) was added to a mixture of HI (30 g) and acetic acid (20 g). The mixture was heated to 100° C. overnight. After cooling it was poured into a cold sodium thiosulphate solution (150 mL, 10%) and extracted using CH2Cl2. The combined organic extracts were dried (MgSO4) and evaporated to give a white solid. The crude product was recrystallised from diethyl ether. Yield: 4.8 g (64%)

Workup

  1. temperatureAfter cooling it
  2. extractionextracted
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customevaporated
  5. customto give a white solid
  6. customThe crude product was recrystallised from diethyl ether

Sources & evidence

ORD record
ord-5e69fe56e7e042fd9f6eb6361228f83f
Source dataset
uspto-grants-2002_09
Patent number
US06447656B1

Linked notes

Loading…