3-(Benzyloxy)phenol Chemical Properties

Melting point:

50°C

Boiling point:

200 °C / 5mmHg

Density 

1.0907 (rough estimate)

refractive index 

1.5906 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

9.59±0.10(Predicted)

color 

White to Almost white

CAS DataBase Reference

3769-41-3

NIST Chemistry Reference

Benzyl 3-hydroxyphenyl ether(3769-41-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41

Safety Statements 

26-36/37/39-39

HS Code 

29095000

3-(Benzyloxy)phenol Usage And Synthesis

Chemical Properties

White solid

Uses

3-(Benzyloxy)phenol is an isomer of benzyloxyphenol (BLP), which contains the structures 2-BLP, 3-BLP, and 4-BLP. 3-BLP is used for chromatographic identification or isomer extraction and separation studies.

Synthesis

General procedure for the preparation of 3-benzyloxyphenol: Resorcinol (10.0 g, 90.9 mmol) was dissolved in acetone (50 mL) and cooled to 5-10 °C. With continuous stirring, anhydrous potassium carbonate (18.8 g, 136.3 mmol) was added. Maintaining this temperature, benzyl bromide (10.88 g, 63.6 mmol) was added slowly and the cooling bath was removed after 10 minutes. The reaction mixture was refluxed for 12 to 17 hours. After the temperature was reduced to 20 to 40°C, the solid potassium carbonate was removed by filtration. The filtrate was concentrated, poured into ice water, acidified with 6N hydrochloric acid and subsequently extracted with ethyl acetate (3 x 25 mL). The organic layers were combined, washed with water, dried over anhydrous sodium sulfate and evaporated to give a brown colloidal substance. Purification by column chromatography (230-400 mesh silica gel, eluent ethyl acetate:petroleum ether = 10:90), discarding the dibenzyloxyditerpene by-product, gave pure light brown colloidal target product 3-benzyloxyphenol. Yield: 13.5 g, 68% yield. Product characterization data: 1H NMR (CDCl3, 200MHz): δ 7.50-7.30 (m, 5H), 7.12 (t, J = 8.2Hz, 1H), 6.57 (dd, J = 1.8, 6.2Hz, 1H), 6.50-6.40 (m, 2H), 5.02 (s, 2H), 4.86 (bs, 1H, D2O exchangeable). Mass spectrum (CI): m/z 201 (M++1). IR (KBr, cm-1): 3406, 3032, 1595, 1490, 1454.

References

[1] Patent: US2014/256657, 2014, A1. Location in patent: Paragraph 0399
[2] Tetrahedron, 2007, vol. 63, # 43, p. 10698 - 10708
[3] Journal of Organic Chemistry, 1997, vol. 62, # 10, p. 3062 - 3075
[4] Journal of Medicinal Chemistry, 2004, vol. 47, # 17, p. 4155 - 4158
[5] Chemical Communications, 2018, vol. 54, # 39, p. 4935 - 4938

3-(Benzyloxy)phenol(3769-41-3)Related Product Information

• Butylated hydroxyanisole
• 3-Bromophenol
• 3-Aminophenol
• Triclosan
• Monobenzone
• m-Anisyl alcohol
• 2-Ethoxyphenol
• 1,3-Dimethoxybenzene
• Benzylparaben
• 3-Hydroxybenzoic acid
• Guaiacol
• 4-Methoxybenzylchloride
• 3'-Hydroxypropiophenone
• 2-Phenylphenol
• Resorcinol
• Methylparaben
• 4-Hydroxybenzoic acid
• 4-Methoxyphenol