Water → HCID 86689986, compound

HRID 1754053Notes

Reaction equation

HRID 1754053 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([OH:5])=[O:4].[CH2:10]([OH:24])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C1(C)C=C[C:28]([S:31](O)(=O)=O)=CC=1.[OH2:36].[C:37]1(C)C=C[CH:40]=[CH:39][CH:38]=1>C(OCC)(=O)C>[OH:1][CH:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([O:5][CH:38]([CH2:39][CH2:40][S:31][CH3:28])[C:37](=[O:36])[O:24][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][CH3:23])=[O:4]

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 82091-TetradecanolHCID 11427alpha-Hydroxy-gamma-methylmercaptobutyric acid

Product 1

HCID 86689986HCID 86689986, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 2-hydroxy-4-(methylthio)butanoic acid (Alimet 88%) (10.1 g, 59.2 mmol) was added 1-tetradecanol (7.57 g, 35.3 mmol), p-toluenesulfonic acid (0.55 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 oil. The oil was purified by silica gel chromatography with 0-30% ethyl acetate/heptane to give a light yellow oil (3.34 g, 24%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.85 (t, J=6.83 Hz, 3 H) 1.11-1.38 (m, 22 H) 1.56 (t, J=6.20 Hz, 2 H) 1.76-1.99 (m, 2 H) 1.99-2.10 (m, 8 H) 2.51-2.64 (m, 4 H) 3.99-4.15 (m, 2 H) 4.16-4.32 (m, 1 H) 5.00-5.16 (m, 1 H) 5.51-5.69 (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 oil
  9. customThe oil was purified by silica gel chromatography with 0-30% ethyl acetate/heptane

Sources & evidence

ORD record
ord-82697acceb8a4b98a1a702ddb8f37f63
Source dataset
uspto-grants-2015_10
Patent number
US09169203B2

Reaction notes

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