Pyridine → HCID 18315379, compound

HRID 275870Notes

Reaction equation

HRID 275870 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17]O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][Cl:21])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 27640763-[4-(Benzyloxy)phenyl]propan-1-ol

Product 1

HCID 18315379HCID 18315379, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

3-(4-Benzyloxyphenyl)propanol produced in Example 193-(1) (1.5 g) was dissolved in toluene (30 ml). To the solution were added thionyl chloride (0.88 g) and pyridine (0.1 ml). The mixture was stirred for 2 hours at 80° C. The reaction mixture was cooled, to which was added saturated sodium hydrogencarbonate to cause decomposition, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 3-(4-benzyloxyphenyl)propyl chloride (1.3 g) as a colorless crystalline product. m.p.: 34-35° C.

Workup

  1. temperatureThe reaction mixture was cooled, to which
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-0f71485f24914ebab08cfba6da9d1543
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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