5-Hydroxy-2-methoxybenzaldehyde

5-Hydroxy-2-methoxybenzaldehyde Property

Melting point:

110-115 °C

Boiling point:

309.0±22.0 °C(Predicted)

Density 

1.231±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Acetone (Slightly), DMSO (Slightly)

pka

9.73±0.18(Predicted)

form 

Solid

color 

Light Brown to Dark Orange

Stability:

Air Sensitive

Safety

Hazard Codes 

Xi

HazardClass 

IRRITANT, AIR SENSITIVE

HS Code 

2916399090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

5-Hydroxy-2-methoxybenzaldehyde Chemical Properties,Usage,Production

Uses

5-Hydroxy-2-methoxy-benzaldehyde is a phenolic substance that can be used in organic synthesis.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 2437, 1974 DOI: 10.1021/jo00930a032

Synthesis

The general procedure for the synthesis of 5-hydroxy-2-methoxybenzaldehyde from 2-methoxy-5-(methoxymethoxy)benzaldehyde was as follows: to a solution of 2-methoxy-5-(methoxymethoxy)benzaldehyde (33.5 g, 0.17 mol, 1 eq.) in tetrahydrofuran (THF, 150 mL) was added 3N hydrochloric acid (HCl, 250 mL, 4.4 eq.). The reaction mixture was stirred at 50 °C for 1 h, subsequently cooled to room temperature and diluted with deionized water (500 mL). The mixture was neutralized to pH 7-8 with solid potassium carbonate (K2CO3). the light yellow solid product was collected by filtration, washed with deionized water and dried to afford 5-hydroxy-2-methoxybenzaldehyde (17.9 g, 74.6% yield) as a light yellow solid. The product was confirmed by NMR hydrogen spectrum (400 MHz, DMSO-d6): δ= 10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H). Low resolution mass spectrometry (LRMS) showed the molecular ion peak (M+H+) m/z 154.0.

References

[1] Patent: WO2013/102142, 2013, A1. Location in patent: Paragraph 0193
[2] Patent: WO2013/102142, 2013, A1. Location in patent: Paragraph 0172