ChemicalBook CAS DataBase List 3-TERT-BUTYL-2-HYDROXYBENZALDEHYDE

3-TERT-BUTYL-2-HYDROXYBENZALDEHYDE synthesis

7synthesis methods

Product Name:3-TERT-BUTYL-2-HYDROXYBENZALDEHYDE
CAS Number:24623-65-2
Molecular formula:C11H14O2
Molecular Weight:178.23

3-Tert-butyl-2-hydroxybenzaldehyde can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly in laboratory research and development process. It can be synthesized by the oxidation of 2-tert-butylphenol, magnesium chloride and paraformaldehyde.

50-00-0 Synthesis

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Yield:24623-65-2 90%

Reaction Conditions:

with triethylamine;magnesium chloride in tetrahydrofuran for 3 h;Heating / reflux;

Steps:

3
To a stirred suspension of 2-tert-butylphenol (6)(4.55g, 30 mmol), magnesium chloride (5.71 g, 60 mmol) and paraformaldehyde (2.08 g, 66 mmol) in THF (120 mL) at room temperature, was added triethylamine (8.35 mL, 60 mmol) dropwise. The reaction was heated to reflux for 3 hours to give an orange suspension. The crude was extracted using EtOAc (3*50 mL). A small amount of diluted HCI can be added if a permanent emulsion is formed. The organic layers were dried over MgSO₄ and the volatiles evaporated under low pressure to yield a pale yellow oil which did not need any further purification. It can become dark green on storage. Yield: 90%. Pale yellow oil. ¹H-NMR δ_H (CDpI₃, 300 MHz): 1.44 (9H, s, 3^χCH₃), 6.97 (1 H, t, J = 7.5 Hz, H_AT), 7.41 (1 H, dd, J = 1.5 Hz, J = 7.5 Hz, H_Ar), 7.54 (1 H, dd, J = 1.2 Hz, J = 7.5 Hz, H_Ar), 9.88 (1 H, s, CHO), 11.82 (1 H, s, OH).

References:

UNIVERSITY OF NEWCASTLE UPON TYNE WO2008/132474, 2008, A1 Location in patent:Page/Page column 31

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88-18-6
189 suppliers
$16.00/25mL