Thionyl Chloride → 4-(4,5-Dihydro-1,3-oxazol-2-yl)phenol

HRID 1030676Notes

Reaction equation

HRID 1030676 reaction equation
O[CH2:2][CH2:3][NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.S(Cl)(Cl)=O>C(OCC)(=O)C>[OH:12][C:9]1[CH:8]=[CH:7][C:6]([C:5]2[O:13][CH2:2][CH2:3][N:4]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 156588N-(2-Hydroxyethyl)-4-hydroxybenzamide

Product 1

HCID 1012874-(4,5-Dihydro-1,3-oxazol-2-yl)phenolYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a slurry of 18.0g (0.1 moles) of N-(2-hydroxyethyl)-p-hydroxybenzamide in 100 ml of ethyl acetate was added a solution of 23.80g (0.2 moles) of thionyl chloride in 25 ml of ethyl acetate. Thionyl chloride addition was slow enough to maintain the reaction temperature below 50° C. After 2 hours at room temperature the precipitate was collected by vacuum filtration and then dissolved in 200 ml of water. The solution was neutralized with 5% sodium hydroxide solution. The white precipitate which formed was collected by vacuum filtration and then dried in a vacuum oven at ≈70° C. overnight. This material was identified by NMR and IR spectroscopy as the desired 2-(p-hydroxyphenyl)-oxazoline. An 87% yield was obtained.

Workup

  1. temperatureto maintain the reaction temperature below 50° C
  2. filtrationAfter 2 hours at room temperature the precipitate was collected by vacuum filtration
  3. dissolutiondissolved in 200 ml of water
  4. customThe white precipitate which formed
  5. filtrationwas collected by vacuum filtration
  6. customdried in a vacuum oven at ≈70° C. overnight
  7. customAn 87% yield was obtained

Sources & evidence

ORD record
ord-b4b01278c5c74966a9f2cf33e9796314
Source dataset
uspto-grants-1992_04
Patent number
US05106921

Reaction notes

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