Methylparaben → HCID 136388021, compound

HRID 1365108Notes

Reaction equation

HRID 1365108 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=O)=[CH:4][CH:3]=1.[NH2:12][C@H:13](CO)[CH:14]([CH3:16])[CH3:15]>ClC1C=CC=CC=1>[CH:14]([C@H:13]1[CH2:9][O:8][C:6]([C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)=[N:12]1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 7456MethylparabenHCID 640993L-Valinol

Product 1

HCID 136388021HCID 136388021, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Under an argon atmosphere, a mixture of methyl 4-hydroxybenzoate (1.5 mmol), (L)-valinol (1.8 mmol), Zn4(OCOCF3)6O (0.15 mmol) and chlorobenzene (2.5 mL) was heated under reflux for 12 hours. From the resulting solution, the solvent was removed using an evaporator, and the residues were purified by silica gel column chromatography to give (S)-4-isopropyl-2-(4-hydroxyphenyl)-1,3-oxazoline in 58% yield. The compound was identified by comparison with physical property data of the known compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. customFrom the resulting solution, the solvent was removed
  4. customan evaporator
  5. customthe residues were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f45cd7dc568a479a8baa32e0a989bc40
Source dataset
uspto-grants-2011_02
Patent number
US07888513B2

Reaction notes

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