Hydrochloric Acid → 16-Mercaptohexadecanoic acid

HRID 1279135Notes

Reaction equation

HRID 1279135 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18].NC(N)=[S:22].[OH-].[Na+].Cl>C(O)C>[SH:22][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4111116-Iodohexadecanoic acidHCID 2723790Thiourea

Product 1

HCID 352258516-Mercaptohexadecanoic acidYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 16-iodohexadecanoic acid (6) (4.0 g, 10.4 mmol) and thiourea (0.88 g, 1.1 equiv.) in ethanol (100 mL) was refluxed overnight under N2 atmosphere. The solution was cooled to room temperature. Sodium hydroxide (1.0 g in 10 mL of water) wad added and the mixture was further heated for 2 hr. After cooling to room temperature 1N HCl was added and the product was extracted using CH2Cl2. The organic extract was dried and evaporated to give a white solid Yield: 2.1 g (69%)

Workup

  1. temperaturewas refluxed overnight under N2 atmosphere
  2. temperaturethe mixture was further heated for 2 hr
  3. additionwas added
  4. extractionthe product was extracted
  5. extractionThe organic extract
  6. customwas dried
  7. customevaporated

Sources & evidence

ORD record
ord-48dae631f1574782807114973786c7b2
Source dataset
uspto-grants-2002_09
Patent number
US06447656B1

Reaction notes

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