Toluene → HCID 9835091, compound

HRID 1086526Notes

Reaction equation

HRID 1086526 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:18](O)CCCCC(C)C>>[C:1]([O:10][CH2:18][CH:14]([CH2:13][CH3:12])[CH2:15][CH2:16][CH2:11][CH3:17])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4]

Participants

4

Reactant 3

HCID 1140TolueneHCID 54432-Mercaptobenzoic AcidHCID 15450Isooctan-1-ol

Product 1

HCID 9835091HCID 9835091, compound

Procedure

77.1 g (0.5 mol) of thiosalicylic acid are dissolved, with stirring, in 250 ml of hot isooctanol. After the addition of 100 ml of toluene and a catalytic amount of paratoluenesulfonic acid, the reaction mixture is heated under reflux. Under azeotropic conditions, 8.5 ml of water (calculated: 9 ml) separate off after 25 hours. The residue is extracted by shaking with a bicarbonate solution, then washed with water and dried. The volatile constituents are removed in vacuo. The product is obtained after rectification with a mercury diffusion pump.

Workup

  1. temperaturea catalytic amount of paratoluenesulfonic acid, the reaction mixture is heated
  2. temperatureunder reflux
  3. customUnder azeotropic conditions, 8.5 ml of water (calculated: 9 ml) separate off after 25 hours
  4. extractionThe residue is extracted
  5. washwashed with water
  6. customdried
  7. customThe volatile constituents are removed in vacuo

Sources & evidence

ORD record
ord-6c5627f96c7c43209f8868d819b57756
Source dataset
uspto-grants-1991_07
Patent number
US05030671

Reaction notes

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