Benzyl Alcohol → HCID 19802321, compound

HRID 1645783Notes

Reaction equation

HRID 1645783 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][CH2:12][CH:13]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:14]([OH:16])=[O:15].[CH2:22](O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[CH2:22]([O:20][C:19]([CH2:18][CH2:17][CH:13]([CH2:12][S:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:14]([OH:16])=[O:15])=[O:21])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 15234818HCID 15234818, compound

Product 1

HCID 19802321HCID 19802321, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2-naphthylthiomethyl)glutaric acid (14.0 g) in acetonitrile (180 ml) was added benzyl alcohol (57 ml) followed by p-toluenesulfonic acid (0.52 g), and the mixture was refluxed for 23 hours. The reaction mixture was concentrated in vacuo, and the resulting residue was purified by flash column chromatography on silica eluting with dichloromethane/methanol (70:1), and recrystallized from ethyl acetate-hexane to give 11.0 g of 2-(2-benzyloxycarbonylethyl)-3-(2-naphthylthio)propionic acid.

Workup

  1. temperaturethe mixture was refluxed for 23 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe resulting residue was purified by flash column chromatography on silica eluting with dichloromethane/methanol (70:1)
  4. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-761939480b604edda70d2afed34702bf
Source dataset
uspto-grants-1993_01
Patent number
US05177069

Reaction notes

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