Sodium Hydroxide → [2-Bromo-5-(hydroxymethyl)phenyl]methanol

Temperature

10 °C

An about 93:7 mixture (36.7 g) of 2,4-bis(acetoxymethyl)-bromobenzene and 2,6-bis(acetoxymethyl)bromobenzene was dissolved in methanol (183 ml) and cooled to 10° C. To this solution was added dropwise 10% aqueous sodium hydroxide solution (133 g). The reaction mixture was stirred at room temperature for 1 hr, and the solvent (about 200 ml) was evaporated. The residue was neutralized with dilute hydrochloric acid (about 200 ml). To the neutralized solution was added toluene (150 ml) and the mixture was stirred at 80-85° C. for 1 hr and cooled. The resulting crystals were collected by filtration and dried under reduced pressure to give an about 93:7 mixture (22.2 g, 83.7%) of 2,4-bis(hydroxymethyl)bromobenzene and 2,6-bis(hydroxymethyl)-bromobenzene as almost white crystals. 2,4-bis(Hydroxymethyl)-bromobenzene was isolated by preparative HPLC and used in the measurement.

1. customthe solvent (about 200 ml) was evaporated
2. additionTo the neutralized solution was added toluene (150 ml)
3. stirringthe mixture was stirred at 80-85° C. for 1 hr
4. temperaturecooled
5. filtrationThe resulting crystals were collected by filtration
6. customdried under reduced pressure

ORD record

ord-b85aaf49b47f46db959e279794be40f2

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310222B1