Hydrochloric Acid → 9-Oxa-12-thiatetradecanoic acid

HRID 1898780Notes

Reaction equation

HRID 1898780 reaction equation
C([O:3][C:4]([CH:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][S:21][CH2:22][CH3:23])C(OCC)=O)=[O:5])C.Cl>[OH-].[Na+]>[C:4]([OH:5])(=[O:3])[CH2:6][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][S:21][CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23372470Ethyl 2-ethoxycarbonyl9-oxa-12-thiatetradecanoate

Product 1

HCID 150201409-Oxa-12-thiatetradecanoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of the above ethyl 2-ethoxycarbonyl-9-oxa-12-thiatetradecanoate (2 g, 5.8 mmol) in 20% NaOH (10 mL) was refluxed for 6 h. The solution was acidified with HCl (pH 2), and extracted with ethyl acetate (120 mL). The organic phase was washed with water (2×30 mL), brine (30 mL) and dried (Na2SO4). After evaporation of the solvent, the resulting product was heated on an oil bath at 180° to 200° C. for 15 min. The crude product was purified by Kugelrohr distillation to afford the title compound, 9-oxa-12-thiatetradecanoic acid (1.4 g, 98%); bp 121°-125° C./0.005 torr; IR(neat):3020 (broad) and 1730 cm-1 ; NMR: 1.27 (3H, t, J=7.7 Hz), 1.34 (6H, m), 1.53-1.68 (4H, m), 2.36 (2H, t, J=7.1 Hz), 2.58 (2H, q, J=7.7 Hz), 2.71 (2H, t, J=7 Hz), 3.45 (2H, t, J=6.8 Hz), 3.59 (2H, t, J=7 Hz), and 10.6 ppm (1H, br s); Found: C, 58.11, H, 9.8%. Calcd for C12H24SO3 : C, 58.03, H, 9.74%.

Workup

  1. extractionextracted with ethyl acetate (120 mL)
  2. washThe organic phase was washed with water (2×30 mL), brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. customAfter evaporation of the solvent
  5. temperaturethe resulting product was heated on an oil bath at 180° to 200° C. for 15 min
  6. distillationThe crude product was purified by Kugelrohr distillation

Sources & evidence

ORD record
ord-4896e5b63caa4314ac72b4c8438dc1d3
Source dataset
uspto-grants-1996_11
Patent number
US05571689

Reaction notes

Loading…