Hydrochloric Acid → 11-Mercaptoundecanoic Acid

HRID 1279131Notes

Reaction equation

HRID 1279131 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].NC(N)=[S:17].[OH-].[Na+].Cl>C(O)C.O>[SH:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1781211-Bromoundecanoic acidHCID 2723790Thiourea

Product 1

HCID 54350211-Mercaptoundecanoic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

11-Bromoundecanoic acid (20.0 g, 0.075 mol) and thiourea (6.3 g, 1.1 equiv.) were refluxed in ethanol (250 mL) overnight. Sodium hydroxide (6.3 g) in water (20 mL) was added and the mixture was further refluxed for 2 hr. The solution was cooled and acidified with 1N HCl. Ethanol was evaporated under reduced pressure and the aqueous residue was extracted With CH2Cl2. The combined organic extracts were dried (MgSO4) and evaporated to give white powder. Yield: 15.0 g (91%)

Workup

  1. temperaturethe mixture was further refluxed for 2 hr
  2. temperatureThe solution was cooled
  3. customEthanol was evaporated under reduced pressure
  4. extractionthe aqueous residue was extracted With CH2Cl2
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customevaporated
  7. customto give white powder

Sources & evidence

ORD record
ord-f10b5cbe561742e1a6945984d3336563
Source dataset
uspto-grants-2002_09
Patent number
US06447656B1

Reaction notes

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