Hydrochloric Acid → HCID 15020141, compound

HRID 1898782Notes

Reaction equation

HRID 1898782 reaction equation
[OH-].[Na+].[C:3]([O:18]CC)(=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][O:14][CH2:15][CH3:16].Cl>CO>[C:3]([OH:18])(=[O:17])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][S:11][CH2:12][CH2:13][O:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15020144HCID 15020144, compound

Product 1

HCID 15020141HCID 15020141, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH (1M, 24 mL, 24 mmol) was added to a solution of the above ethyl 9-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, 9-thia-12-oxatetradecanoic acid; yield 92%; bp 134°-136° C./0.005 torr; IR (neat): 3000 (broad) and 1735 cm-1NMR: 1.23 (3H, t, J=7.2 Hz), 1.28-1.46 (6H, m), 1.53-1.68 (4H, m), 2.35 (2H, t, J=7.3 Hz), 2.54 (2H, t, J=7.1 Hz), 2.70 (2H, t, J=7.1 Hz), 3.52 (2H, q, J=7.2 Hz), 3.60 (2H, t, J=6.9 Hz), and 8.85 ppm (1H, br s); Found: C, 57.96, H, 9.77%. Calcd for C12H24SO3 : 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-d6d4679542854f5faefb0019b4f58361
Source dataset
uspto-grants-1996_11
Patent number
US05571689

Reaction notes

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