Water → HCID 86689987, compound

HRID 1754054Notes

Reaction equation

HRID 1754054 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([OH:5])=[O:4].[CH2:10]([OH:26])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1(C)C=C[C:30]([S:33](O)(=O)=O)=CC=1.[OH2:38].[C:39]1(C)C=C[CH:42]=[CH:41][CH:40]=1>C(OCC)(=O)C>[OH:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([O:5][CH:40]([CH2:41][CH2:42][S:33][CH3:30])[C:39]([O:26][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:38])=[O:4]

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 2682Cetyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 11427alpha-Hydroxy-gamma-methylmercaptobutyric acid

Product 1

HCID 86689987HCID 86689987, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2-hydroxy-4-(methylthio)butanoic acid (Alimet 88%) (10.0 g, 58.6 mmol) was added 1-hexadecanol (8.55 g, 35.3 mmol), p-toluenesulfonic acid (0.56 g, 2.9 mmol) in toluene (50 mL) in a round bottom flask that was fitted with a Dean Stark trap and reflux condenser. The resulting mixture was heated to reflux with removal of water overnight. The reaction was cooled to room temperature and then diluted with ethyl acetate (65 mL) and washed with sat. NaHCO3 (3×30 mL), water (1×30 mL), dried over magnesium sulfate, filtered and evaporated to give a dark brown oil. The oil was purified by silica gel chromatography with 0-30% ethyl acetate/heptane to give a light yellow oil (3.2 g, 22%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.85 (t, J=6.68 Hz, 3 H) 1.10-1.35 (m, 26 H) 1.48-1.64 (m, 2 H) 1.76-1.98 (m, 2 H) 1.99-2.12 (m, 8 H) 2.50-2.66 (m, 4 H) 4.01-4.18 (m, 2 H) 4.17-4.32 (m, 1 H) 5.00-5.15 (m, 1 H) 5.54-5.72 (m, 1 H).

Workup

  1. customwas fitted with a Dean Stark trap
  2. temperaturereflux condenser
  3. temperatureThe resulting mixture was heated
  4. washwashed with sat. NaHCO3 (3×30 mL), water (1×30 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a dark brown oil
  9. customThe oil was purified by silica gel chromatography with 0-30% ethyl acetate/heptane

Sources & evidence

ORD record
ord-c2fa25b194be49d38bcd7778946243e5
Source dataset
uspto-grants-2015_10
Patent number
US09169203B2

Reaction notes

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