p-Toluenesulfonic acid → HCID 56949563, compound

HRID 43305Notes

Reaction equation

HRID 43305 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])/[C:2](=[CH:4]/[CH3:5])/[CH3:3].[C:10]([OH:13])(=[S:12])[CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(OCC)C>[C:10]([S:12][CH:4]([CH3:5])[CH:2]([CH3:3])[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:13])[CH3:11]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 5281163Ethyl tiglateHCID 178418634HCID 178418634, compound

Product 1

HCID 56949563HCID 56949563, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 51.27 g (0.40 mol) of ethyl tiglate, 76.12 g (1.00 mol) of thioacetic acid, and 7.60 g (0.04 mol) of para-toluenesulfonic acid was stirred under nitrogen atmosphere at 75° C. for 24 hours. After cooling, diethyl ether and a saturated aqueous sodium bicarbonate solution were added to the reaction mixture. The organic layer was separated and washed twice with brine. The solvent in the organic layer was evaporated off, and vacuum distillation (68 to 71° C./2 torr) was performed to give 76.36 g of the objective compound (GC purity: 98.3%, yield: 91.8%, diastereomer ratio: 80.9/19.1).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed twice with brine
  4. customThe solvent in the organic layer was evaporated off
  5. distillationvacuum distillation (68 to 71° C./2 torr)

Sources & evidence

ORD record
ord-016ffa8300174900b07aef8aef472a85
Source dataset
uspto-grants-2013_09
Patent number
US08536364B2

Reaction notes

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