Benzyl Alcohol → HCID 59706550, compound

HRID 418757Notes

Reaction equation

HRID 418757 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:3]=1.[CH2:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 666489023-(Pyridin-3-yl)propanoic acid--hydrogen chloride (1/1)

Product 1

HCID 59706550HCID 59706550, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of 3-(3-pyridyl)propionic acid hydrochloride (1.51 g, 10.0 mmol) in benzyl alcohol (3.1 mL, 30 mmol) was added p-toluenesulfonic acid monohydrate (181.8 mg, 0.96 mmol), and the mixture was stirred at 130° C. for 20 h. The reaction mixture was diluted with ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution was added to separate the phases. The aqueous layer was extracted again with ethyl acetate, and the combined organic layer was concentrated with reduced pressure. The residue was subjected to silica gel column chromatography (hexane-ethyl acetate1:1→1:3) to give 1.69 g of the title compound as oil (yield: 70%).

Workup

  1. customto separate the phases
  2. extractionThe aqueous layer was extracted again with ethyl acetate
  3. concentrationthe combined organic layer was concentrated with reduced pressure

Sources & evidence

ORD record
ord-5af85d1e3534405d97cd706d5a1cafa7
Source dataset
uspto-grants-2012_01
Patent number
US08093294B2

Reaction notes

Loading…