4-Hydroxybenzyl Alcohol → 4-(5-Methyl-2-phenyl-4-oxazolylmethoxy)benzyl alcohol

HRID 1059092Notes

Reaction equation

Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:8][C:7]1[O:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][C:3]=1[CH2:2][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole (5.00 g), parahydroxybenzyl alcohol (3.29 g) and potassium carbonate (6.66 g) were suspended in dimethylformamide (25 ml) and the suspension was stirred at 50° C. for 3.5 hr. The reaction mixture was cooled and water (25 ml) was added at not higher than 15° C. The mixture was stirred for about 5 min and at about 5° C. for 1 hr under ice-cooling. The crystals were collected by filtration, washed twice with water (15 ml) and dried under reduced pressure at 50° C. to give the objective product (6.85 g) in a yield of 96%.

Workup

temperatureThe reaction mixture was cooled
stirringThe mixture was stirred for about 5 min and at about 5° C. for 1 hr under ice-
temperaturecooling
filtrationThe crystals were collected by filtration
washwashed twice with water (15 ml)
customdried under reduced pressure at 50° C.

Sources & evidence

ORD record: ord-c544ab93ed3b4072996b34a72e98371f
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518435B1

Reaction notes

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