Toluene → 2-Thiopheneethanol tosylate

HRID 875250Notes

Reaction equation

HRID 875250 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:24][CH2:25][OH:26]>C(N(CC)CC)C>[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:24][CH2:25][O:26][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 1140TolueneHCID 73974-Toluenesulfonyl chlorideHCID 794002-Thiopheneethanol

Product 1

HCID 36820342-Thiopheneethanol tosylate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
45 °C

Procedure

4-toluenesulfonyl chloride (162 g), toluene (363.3 g) and 2-(2-Thienyl)ethanol (104 g) are combined. Triethylamine (93 g) is added maintaining the temperature lower than 45° C. After 4 hrs, the mixture is washed with aqueous phosphoric acid, aqueous sodium hydroxide and then water. The organic phase is distilled off under vacuum. Isopropanol (314 g) and heptanes (365.9 g) are added. The batch is crystallized by cooling and isolated at −15° C. The crystals are filtered and washed with heptanes (175 mL). The crystals are then dried under vacuum at room temperature until a melting point of 30° C. is obtained.

Workup

  1. washthe mixture is washed with aqueous phosphoric acid, aqueous sodium hydroxide
  2. distillationThe organic phase is distilled off under vacuum
  3. additionIsopropanol (314 g) and heptanes (365.9 g) are added
  4. customThe batch is crystallized
  5. temperatureby cooling
  6. customisolated at −15° C
  7. filtrationThe crystals are filtered
  8. washwashed with heptanes (175 mL)
  9. customThe crystals are then dried under vacuum at room temperature until a melting point of 30° C.
  10. customis obtained

Sources & evidence

ORD record
ord-d39a6ae4bfcc44b1b338adc147ac8848
Source dataset
uspto-grants-2015_03
Patent number
US08981121B2

Reaction notes

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