3-TERT-BUTYL-2-HYDROXYBENZALDEHYDE Chemical Properties

Boiling point:

78-79 °C/1 mmHg (lit.)

Density 

1.041 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.544(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Soluble), DMSO (Sparingly)

form 

Oil

pka

9.55±0.10(Predicted)

color 

Pale Yellow to Light Yellow

InChI

InChI=1S/C11H14O2/c1-11(2,3)9-6-4-5-8(7-12)10(9)13/h4-7,13H,1-3H3

InChIKey

ROILLNJICXGZQQ-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=CC(C(C)(C)C)=C1O

EPA Substance Registry System

Benzaldehyde, 3-(1,1-dimethylethyl)-2-hydroxy- (24623-65-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29125000

MSDS

• Language:English Provider:SigmaAldrich

3-TERT-BUTYL-2-HYDROXYBENZALDEHYDE Usage And Synthesis

Chemical Properties

light yellow liquid

Uses

3-tert-Butyl-2-hydroxybenzaldehyde is used in preparation of coumarin derivative.

General Description

3-tert-Butyl-2-hydroxybenzaldehyde is a mono-tert-butyl substituted 2-hydroxybenzaldehyde that can be synthesized using ethylbromide and 2-tert-butylphenol.

Synthesis

Triethylamine (8.35 mL, 60 mmol) was added dropwise to a stirred suspension of 2-tert-butylphenol (4.55 g, 30 mmol), magnesium chloride (5.71 g, 60 mmol) and paraformaldehyde (2.08 g, 66 mmol) in THF (120 mL) at room temperature. The reaction mixture was heated to reflux with continuous stirring for 3 h. An orange-colored suspension was obtained upon completion of the reaction. The crude product was extracted with EtOAc (3 x 50 mL). If a permanent emulsion is formed, a small amount of diluted HCl is added to break the emulsion. The organic layers were combined, dried with anhydrous MgSO4, filtered and concentrated under reduced pressure to give a light yellow oily product which did not require further purification. The product may gradually change to dark green color during storage. Yield: 90%. The product was a light yellow oil.1H-NMR (CDCl3, 300 MHz) δH: 1.44 (9H, s, 3×CH3), 6.97 (1H, t, J = 7.5 Hz, HAr), 7.41 (1H, dd, J = 1.5 Hz, J = 7.5 Hz, HAr), 7.54 (1H, dd, J = 1.2 Hz, J = 7.5 Hz, HAr), 9.88 (1H, s, CHO), 11.82 (1H, s, OH).

References

[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 7, p. 1658 - 1667
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 22, p. 3990 - 4001
[3] Patent: WO2008/132474, 2008, A1. Location in patent: Page/Page column 31
[4] Advanced Synthesis and Catalysis, 2009, vol. 351, # 9, p. 1325 - 1332
[5] Patent: WO2009/109765, 2009, A1. Location in patent: Page/Page column 27; 28

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