Methyl 4-(hydroxymethyl)benzoate → HCID 67111423, compound

HRID 1365107Notes

Reaction equation

HRID 1365107 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=O)=[CH:5][CH:4]=1.[NH2:13][C@H:14](CO)[CH:15]([CH3:17])[CH3:16]>ClC1C=CC=CC=1>[CH:15]([C@H:14]1[CH2:10][O:9][C:7]([C:6]2[CH:11]=[CH:12][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=2)=[N:13]1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 81325Methyl 4-(hydroxymethyl)benzoateHCID 640993L-Valinol

Product 1

HCID 67111423HCID 67111423, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Under an argon atmosphere, a mixture of methyl 4-hydroxymethylbenzoate (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-hydroxymethylphenyl)-1,3-oxazoline in 66% 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-0abf0fd6a6254c78b1f4ee0cb1d88968
Source dataset
uspto-grants-2011_02
Patent number
US07888513B2

Reaction notes

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