Sulfuric Acid → Octanoic acid, 8-mercapto-

HRID 1081927Notes

Reaction equation

HRID 1081927 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].NC(N)=[S:14].[OH-].[Na+].S(=O)(=O)(O)O>O>[SH:14][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 5482758-Bromooctanoic acidHCID 2723790Thiourea

Product 1

HCID 156289Octanoic acid, 8-mercapto-Yield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g 8-bromooctanoic acid (22.4 mmol), 2.24 g thiourea (29.4 mmol) and 22 ml water were placed in a round botton flask, and the mixture was refluxed for 3 hours. 15.1 ml 3M sodium hydroxide was then added and the mixture was refluxed for one additional hour. The reaction mixture was cooled in an ice bath, and dilute sulfuric acid was added dropwise until the solution had a pH of about 2. The cloudy solution was then extracted with ether (2×25 ml), dried over anhydrous MgSO4, and concentrated under reduced pressure to give a white solid (2.52 g, 64%). 1H-NMR (300 MHz, CDCl3) 1.37, (m, 7 H); 1.60, (m, 4 H); 2.35, (t, J=7.4 Hz, 2 H); 2.52, (q, J=7.4 Hz, 2 H).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperaturethe mixture was refluxed for one additional hour
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. extractionThe cloudy solution was then extracted with ether (2×25 ml)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2bbf4f38e265402b8c9e60e795163629
Source dataset
uspto-grants-1996_12
Patent number
US05587475

Reaction notes

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