Pyridine → Toluene-4-sulfonic acid, 2-benzyloxy-1-methylethyl ester

HRID 2182018Notes

Reaction equation

HRID 2182018 reaction equation
[CH3:1][CH:2]([CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:3].N1C=CC=CC=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>O>[C:7]1([CH2:6][O:5][CH2:4][CH:2]([O:3][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH3:1])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 2959551-(Benzyloxy)propan-2-ol

Product 1

HCID 562182Toluene-4-sulfonic acid, 2-benzyloxy-1-methylethyl esterYield 73.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

CH3CH(OH)CH2OCH2Ph (50.0 g) and pyridine (150 ml) were put into a flask, and under cooling with ice, p-toluenesulfonic acid chloride (63.2 g) was added over a period of 30 minutes. The mixture was stirred at room temperature for 4 days, and then water (150 ml) was added, followed by extraction twice with dichloromethane (100 ml). The extracted organic phase was washed twice with a KHCO3 saturated aqueous solution (100 ml) and twice with water (100 ml), dried over magnesium sulfate, filtered and further concentrated to obtain PhCH2OCH2CH(CH3)OTs (71.2 g).

Workup

  1. additionwas added over a period of 30 minutes
  2. extractionfollowed by extraction twice with dichloromethane (100 ml)
  3. washThe extracted organic phase was washed twice with a KHCO3 saturated aqueous solution (100 ml) and twice with water (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationfurther concentrated

Sources & evidence

ORD record
ord-bdfc74c0f51040658121e1636f6d71e0
Source dataset
uspto-grants-2005_05
Patent number
US06894187B2

Reaction notes

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