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

HRID 359810Notes

Reaction equation

HRID 359810 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-87e4c388b3d84b419034f984df586ba1
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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