Hydrochloric Acid → Methyl 2-Benzyl-3-tert-butylmercaptopropionate

HRID 847618Notes

Reaction equation

HRID 847618 reaction equation
[Na].[C:2]([SH:6])([CH3:5])([CH3:4])[CH3:3].[CH2:7]([C:14](=[CH2:19])[C:15]([O:17][CH3:18])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>CO>[CH2:7]([CH:14]([CH2:19][S:6][C:2]([CH3:5])([CH3:4])[CH3:3])[C:15]([O:17][CH3:18])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6387tert-Butyl mercaptanHCID 575761Methyl 2-benzylprop-2-enoateHCID 5360545Sodium

Product 1

HCID 54394236Methyl 2-Benzyl-3-tert-butylmercaptopropionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To sodium (3.05 g, 133 mmol) in methanol (135 ml) was added tert-butylmercaptan (17.0 ml, 151 mmol). After 20 min methyl a-benzylacrylate (17.05 g, 96.8 mmol) in methanol (100 ml) was added and after 1 h at room temperature the mixture was heated at reflux for 17 h. After cooling, the mixture was acidified with 2M HCl (70 ml), concentrated, taken up in ether, washed with water and brine, then dried over MgSO4 and evaporated to 23.59 g (92%) of an oil. 1H NMR (CDCl3) δ 7.15-7.35 (m,5H), 3.63 (s,3H), 2.60-3.05 (m,5H), 1.28 (s,9H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 h
  3. temperatureAfter cooling
  4. concentrationconcentrated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customevaporated to 23.59 g (92%) of an oil

Sources & evidence

ORD record
ord-3f80ed65c4fd464a9ac8266c8da84a54
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

Loading…