ChemicalBook CAS DataBase List 4-Hydroxy-2,6-dimethylbenzoic acid

4-Hydroxy-2,6-dimethylbenzoic acid synthesis

14synthesis methods

Product Name:4-Hydroxy-2,6-dimethylbenzoic acid
CAS Number:75056-97-2
Molecular formula:C9H10O3
Molecular Weight:166.17

Benzoic acid, 2,6-dimethyl-4-(phenylmethoxy)-

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Yield: 40%

Reaction Conditions:

with water;hydrogen bromide;acetic acid at 20; for 1 h;

Steps:

4-Hydroxy-2,6-dimethylbenzoic Acid (12)
Compound 11 (180 mg, 1.08 mmol) was dissolved in HBr (33 wt% in AcOH, 3.5 mL) and left to react at r.t. for 1 h. H₂O was added and the aqueous phase was extracted with EtOAc (3 × 10 mL). The combined organic phases were washed with brine, dried (anhyd MgSO₄), and evaporated in vacuo. The residue was chromatographed (using gradient of 25% of PE in EtOAc until 100% EtOAc to yield 70 mg (40%) of 12; white solid; mp 168-170 °C; R_f = 0.41 (silica gel, EtOAc/PE = 1:2). ¹H NMR (500 MHz, CD₃OD): δ = 6.45 (s, 2 H, H_Ar), 2.28 (s, 6 H, CH₃). ¹³C NMR (125 MHz, CD₃OD): δ = 174.1, 159.2, 138.2, 127.2, 115.4, 20.3. HRMS (ESI-): m/z [M - H]^- calcd for C₉H₉O₃: 165.0546; found: 165.0559.

References:

Coman, Anca G.;Paraschivescu, Codruta C.;Hadade, Niculina D.;Juncu, Andrei;Vlaicu, Ovidiu;Popescu, Costin-Ioan;Matache, Mihaela [Synthesis,2016,vol. 48,# 22,art. no. SS-2016-T0294-OP,p. 3917 - 3923]

37934-89-7 Synthesis