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

HRID 2165395Notes

Reaction equation

HRID 2165395 reaction equation
S(Cl)(Cl)=O.O[CH2:6][CH2:7][NH:8][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1>CCOCC>[OH:16][C:13]1[CH:12]=[CH:11][C:10]([C:9]2[O:17][CH2:6][CH2:7][N:8]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

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

Product 1

HCID 1012874-(4,5-Dihydro-1,3-oxazol-2-yl)phenolYield 118%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride (160 ml) was added to 40 g of N-(2-hydroxyethyl)-4-hydroxybenzamide with evolution of gas. The reaction mixture was ultrasonicated for 1.75 hours, then cooled and diluted with ether. The resulting solid product was collected by filtration, washed with ether and dried overnight in a vacuum oven at 40° C. to give 42.5 g of 4,5-dihydro-2-(4-hydroxyphenyl)oxazole in the form of its hydrochloride salt, m.p. 162°-163° C.

Workup

  1. customThe reaction mixture was ultrasonicated for 1.75 hours
  2. temperaturecooled
  3. filtrationThe resulting solid product was collected by filtration
  4. washwashed with ether
  5. customdried overnight in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-c8a7698555d14984bdb6f054b871b3ec
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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