Identification | Back Directory | [Name]
4-hydroxy-.alpha.,.alpha.-dimethyl-Benzeneacetic acid | [CAS]
29913-51-7 | [Synonyms]
4-Hydroxy-α,α-dimethylbenzeneacetic acid 2-(4-Hydroxyphenyl)-2-methylpropanoicaci 4-Hydroxy-α,α-dimethyl-benzeneacetic acid 2-(4-Hydroxyphenyl)-2-Methylpropanoic acid Benzeneacetic acid, 4-hydroxy-α,α-diMethyl- Benzeneacetic acid, 4-hydroxy-alpha,alpha-diMethyl- 4-hydroxy-.alpha.,.alpha.-dimethyl-Benzeneacetic acid | [Molecular Formula]
C10H12O3 | [MDL Number]
MFCD00995712 | [MOL File]
29913-51-7.mol | [Molecular Weight]
180.2 |
Chemical Properties | Back Directory | [Boiling point ]
345.5±17.0 °C(Predicted) | [density ]
1?+-.0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
4.60±0.10(Predicted) |
Hazard Information | Back Directory | [Synthesis]
Step 24c: Synthesis of 2-(4-hydroxyphenyl)-2-methylpropanoic acid (Compound 0804-27)
2-(4-Methoxyphenyl)-2-methylpropanoic acid (Compound 0803-27) (0.85 g, 4.38 mmol) was mixed with pyridine hydrochloride (2.82 g, 24.40 mmol) and the reaction was heated at 180 °C for 5 hours. After completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted to 6 with dilute hydrochloric acid (1 M), followed by extraction with ethyl acetate. The organic layer was separated, dried with anhydrous sodium sulfate and concentrated to give the target product 0804-27 (0.61 g, 76% yield) as a colorless oil.LCMS detection showed m/z of 181 [M + 1]+.1H NMR (400 MHz, DMSO-d6) data were as follows: δ 1.41 (s, 6H), 6.70 (d, J = 8.8 Hz, 2H) , 7.13 (d, J = 8.8Hz, 2H), 9.28 (s, 1H), 12.16 (s, 1H). | [References]
[1] Journal of Medicinal Chemistry, 1994, vol. 37, # 26, p. 4508 - 4521 [2] Patent: WO2005/121102, 2005, A2. Location in patent: Page/Page column 25-26 [3] Patent: WO2009/36016, 2009, A1. Location in patent: Page/Page column 78c [4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 17, p. 4567 - 4570 [5] Journal of Medicinal Chemistry, 2010, vol. 53, # 16, p. 6129 - 6152 |
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SPIRO PHARMA
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