HCID 68278008, compound → HCID 44121587, compound

HRID 931495Notes

Reaction equation

HRID 931495 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1>Cl.O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[CH:15][CH:16]=2)=[N:4][C:3]=1[CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 68278008HCID 68278008, compound

Product 1

HCID 44121587HCID 44121587, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 4-(5-methyl-4-(p-tolyloxymethyl)oxazol-2-yl)benzoate (1.0 g, 2.97 mmol, 1.00 equiv) in 6N hydrochloric acid (30 mL) was stirred overnight at 90° C. The reaction mixture was diluted with 50 mL of water then extracted with 3×150 mL of ethyl acetate. The combined organic layers was washed with 3×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 0.24 g (25%) of 4-(5-methyl-4-(p-tolyloxymethyl)oxazol-2-yl)benzoic acid as a gray solid. LC-MS: (ES, m/z): 324 [M+H]+, 302, 265, 120. H-NMR: 1HNMR (400 MHz, CDCl3, ppm) δ 8.15-8.13 (d, 2H), 8.06-8.04 (d, 2H), 6.94-6.91 (m, 4H), 3.79 (s, 2H), 2.44 (s, 3H,), 2.26 (s, 3H).

Workup

  1. extractionthen extracted with 3×150 mL of ethyl acetate
  2. washThe combined organic layers was washed with 3×50 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d942e0d06e174690bcbbd26d9069a4ee
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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