Hydrochloric Acid → HCID 15020142, compound

HRID 1898783Notes

Reaction equation

HRID 1898783 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:20])[CH2:7][CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH3:19])C.Cl>CO>[C:6]([OH:20])(=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15020145HCID 15020145, compound

Product 1

HCID 15020142HCID 15020142, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH (1M, 24 mL, 24 mmol) was added to a solution of the above ethyl-6-thia-12-oxatetradecanoate, (6.8 mmol) in MeOH (20 mL). After stirring for 7 h, the reaction mixture was acidified with 10% HCl (pH 1) and extracted with ethyl acetate (2×100 mL). The organic phase was washed with water (50 mL), brine (50 mL), and dried (Na2SO4). The crude product was recrystallized from hexane to afford the title compound, 6-thia-12-oxatetradecanoic acid; yield 82%; bp 144°-146° C./0.01 torr; IR(neat): 3000 (broad) and 1730 cm-1 ; NMR: 1.23 (3H, t, J=7.3 Hz), 1.46 (2H, quint, J=6.9 Hz), 1.55-1.69 (6H, m), 1.74 (2H, quint, J=7.3 Hz), 2.37 (2H, t, J=7.6 Hz), 2.51 (2H, t, J=7 Hz), 2.53 (2H, t, J=7 Hz)m 3,42 (2H, t, J=6.9 Hz), 3.48 (2H, q, J=7.3 Hz), and 10.6 ppm (1H, br s); Found: C, 58.07, H, 9.78%. Calcd for C13H26SO2 : C, 58.03, H, 9.74%.

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. washThe organic phase was washed with water (50 mL), brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-c9650122fd8a4330b5bb847ada66e841
Source dataset
uspto-grants-1996_11
Patent number
US05571689

Reaction notes

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