Sodium Hydroxide → 4-[4-(Hydroxymethyl)-5-methyl-1,3-oxazol-2-yl]benzoic acid

HRID 1526842Notes

Reaction equation

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

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate

Product 1

HCID 682784254-[4-(Hydroxymethyl)-5-methyl-1,3-oxazol-2-yl]benzoic acidYield 72%

Procedure

Method D. Reaction of chloride 2 (500 mg, 1.88 mmol) and aqueous NaOH (2 M, 10 mL, 20 mmol) gave acid 55 (313 mg, 72%) as a cream solid: mp (EtOAc/MeOH) 240-242° C.; 1H NMR δ 13.18 (br s, 1H, CO2H), 8.00-8.06 (m, 4 H, H-2, H-3, H-5, H-6), 5.11 (br s, 1 H, OH), 2.41 (s, 3 H, CH3); MS m/z 234.5 (WE, 100%); HRMS calcd for C12H12NO4: 234.0761. Found: 234.0760.

Sources & evidence

ORD record: ord-0aa403afea9d497fbbf8561a0b3bec33
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085570B2

Reaction notes

Loading…