alpha-methoxy-p-cresol Chemical Properties

Melting point:

82.5-83.5 °C

Boiling point:

147-153 °C(Press: 11 Torr)

Density 

1.5319 g/cm3(Temp: 24 °C)

storage temp. 

Inert atmosphere,Room Temperature

pka

9.84±0.26(Predicted)

InChI

InChI=1S/C8H10O2/c1-10-6-7-2-4-8(9)5-3-7/h2-5,9H,6H2,1H3

InChIKey

AHXXIALEMINDAW-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(COC)C=C1

LogP

1.190 (est)

EPA Substance Registry System

Phenol, 4-(methoxymethyl)- (5355-17-9)

Safety Information

HS Code 

2909500090

alpha-methoxy-p-cresol Usage And Synthesis

Definition

ChEBI: 4-(methoxymethyl)phenol is a member of the class of phenols that is p-cresol in which one of the methyl hydrogens has been replaced by a methoxy group. It has a role as a plant metabolite.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 1939, 1989 DOI: 10.1016/S0040-4039(00)99619-9

Synthesis

Under nitrogen protection, 3.96 g (0.03 mol) of p-hydroxybenzyl alcohol (purchased from Tokyo Chemical Industry Co., Ltd.) was added to a 100 mL three-necked flask equipped with a thermometer, a three-way stopper and a magnetic stirrer, followed by 21 g of methanol (purchased from Nacalai Tesque, Inc.) and two drops of nitromethane (purchased from Nacalai Tesque, Inc.). Under stirring conditions at room temperature, 0.2 g of hydrochloric acid (purchased from Nacalai Tesque, Inc.) was slowly added dropwise, followed by continuous stirring of the reaction mixture for 5 h at 30 °C. The reaction mixture was then analyzed by HPLC. Upon completion of the reaction, HPLC analysis showed 95% area percentage of the target product 4-methoxymethylphenol. To the reaction system, 0.28 g of pyridine (purchased from Nacalai Tesque, Inc.) and 8 g of toluene (purchased from Nacalai Tesque, Inc.) were added for neutralization, followed by concentration under reduced pressure to remove methanol. To the residue 31 g of toluene and 6 g of water were added for extraction and the organic phase was washed with 5 g of water. The resulting organic layer was concentrated, cooled to below 10 °C, and the precipitated crystals were filtered and dried to give 3.53 g (yield: 80%) of colorless crystalline 4-methoxymethylphenol. It was analyzed by HPLC and its purity was 99% (excluding the solvent toluene).

References

[1] Journal of Chemical Research - Part S, 2000, # 6, p. 266 - 268
[2] Journal of Chemical Research - Part S, 2000, # 6, p. 266 - 268
[3] Chemical and pharmaceutical bulletin, 2002, vol. 50, # 3, p. 380 - 383
[4] Patent: JP5747348, 2015, B2. Location in patent: Paragraph 0058-0062; 0066-0070
[5] Journal of Organic Chemistry, 1988, vol. 53, # 18, p. 4263 - 4273

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