Benzyl Alcohol → HCID 59706550, compound

HRID 1774398Notes

Reaction equation

HRID 1774398 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 acetate 1:1→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-3eabb1e45c7f46d7a7a87b4df6f53e7c
Source dataset
uspto-grants-2016_02
Patent number
US09260375B2

Reaction notes

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