Hydrochloric Acid → 3-(p-Vinylbenzylthio)propionic acid

HRID 1886102Notes

Reaction equation

HRID 1886102 reaction equation
[OH-].[K+].C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C.[SH:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23].[CH:25]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1)=[CH2:26].Cl>C(O)C>[CH:25]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31][S:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:29][CH:28]=1)=[CH2:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 65143-Mercaptopropionic AcidHCID 14797Potassium HydroxideHCID 314042,6-Di-tert-butyl-4-methylphenolHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 195971553-(p-Vinylbenzylthio)propionic acidYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of potassium hydroxide (84 g, 1.3 moles) and 2,6-di-tert-butyl-p-cresol (1 g) in ethanol (1.2 liter) at room temperature was added under a nitrogen atmosphere 3-mercaptopropionic acid (65.0 g, 0.61 mole) over 10 minutes. Following addition the solution was stirred an additional hour at room temperature and then p-vinylbenzyl chloride (93 g, 0.6 mole) was added at room temperature over 30 minutes. After addition, the solution was stirred at ambient temperature overnight. The next day the mixture was poured into ice and concentrated hydrochloric acid (150 ml). The solid was filtered and dried on a funnel under vacuum. The solid was dissolved in dichloromethane (1.4 liter), washed with saturated NaCl (200 ml), dried over anhydrous magnesium sulfate, filtered and the solvent removed on a rotary evaporator. The residue was dissolved in diethyl ether (600 ml), hexane (1 liter) was added to the cloud point, and then the mixture was placed in a freezer. The white solid product was collected by filtration: m.p. of 77°-78° C. Yield of 80%. Analysis calculated for C12H14O2S: C, 64.84, H, 6.35, S, 14.42. Found: C, 64.98, H, 6.29, S, 14.02. 1H NMR (CDCl3) δ2.6 (m, 4H, CH2CH2), 3.7 (s, 2H, ArCH2S), 5.15+5.65 (AB quartet, 2H, CH2 =), 6.65 (m, 1H, CH=), 7.3 (m, 4H, ArH's).

Workup

  1. additionaddition the solution
  2. additionAfter addition
  3. stirringthe solution was stirred at ambient temperature overnight
  4. filtrationThe solid was filtered
  5. customdried on a funnel under vacuum
  6. dissolutionThe solid was dissolved in dichloromethane (1.4 liter)
  7. washwashed with saturated NaCl (200 ml)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent removed on a rotary evaporator
  11. dissolutionThe residue was dissolved in diethyl ether (600 ml)
  12. additionhexane (1 liter) was added to the cloud point
  13. filtrationThe white solid product was collected by filtration

Sources & evidence

ORD record
ord-62440f64cab540048b4f6d9b7c9279af
Source dataset
uspto-grants-1992_09
Patent number
US05149737

Reaction notes

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