Hydrochloric Acid → 6,12-Dithiatetradecanoic acid

HRID 1090938Notes

Reaction equation

HRID 1090938 reaction equation
[OH-].[Na+].[C:3]([O:18]CC)(=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:15][CH3:16].O.Cl>CO>[C:3]([OH:18])(=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][S:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15020143Ethyl 6,12-dithiatetradecanoate

Product 1

HCID 98381736,12-Dithiatetradecanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (1 M, 6.2 mL, 6.2 mmol) was added to a solution of ethyl 6,12-dithiatetradecanoate (0.9 g, 3.1 mmol) in MeOH (15 mL). After stirring for 4 hours, water (20 mL) was added and the reaction mixture was acidified (pH 1, HCl) extracted with EtOAc (2×100 mL), and the organic phase was washed with water (20 mL), brine (20 mL), and then dried (Na2SO4). The product crystallized from n-hexane to yield the title compound as a white solid (0.77 g, 95%, mp 49.5° C.-50.0° C.). IR: 3000, 1720 cm-1 ; 1H NMR, 1.23 (t, 3H), 1.49 (quintet, 2H), 1.56-1.68 (m, 6H), 1.74 (quintet, 2H), 2.38 (t, 2H), 2.51 (t, 2H), 2.53 (t, 4H), 2.54 (q, 2H), and 10.45 (b, IH). Anal. Calcd for C12H24S2O2 : C, 54.50; H, 9.15%. Found: C, 54.59; H, 9.21%.

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. washthe organic phase was washed with water (20 mL), brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe product crystallized from n-hexane

Sources & evidence

ORD record
ord-b505f08aa437419690b86139ae0276bb
Source dataset
uspto-grants-1992_01
Patent number
US05082967

Reaction notes

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