Sodium Iodoacetate → (Benzyloxy)acetic acid

Temperature

25 °C

(2,4,6-Trimethyl-phenyl)-methanol (4.50 g, 30 mmol) was introduced to the suspension of sodium hydride (95%, 0.84 g, 35 mmol) in dry THF (100 ml), under a nitrogen blanket and the reaction mixture was heated to reflux for one hour. After the reaction mixture cooled down to 25° C., sodium iodoacetate (7.28 g, 35 mmol) was added in one portion, and the reaction was heated to reflux for another two hours. The resulting precipitate was collected by filtration, and then dissolved into water (60 ml). This aqueous solution was acidified to pH 2 at 5° C. by 6N HCl to generate precipitate, which was then isolated by filtration to give pure benzyloxy acetic acid as white powder (3.2 g, 51.2%), mp 81-83°. Microanalysis for C12H16O3 (208.26): C, 69.21, H, 7.74. found: C, 68.83, H, 7.66. 1H-NMR (d6-DMSO): 6.82 (s, 2 arom. H); 4.50 (s, OCH2CO2H); 4.01, 4.02 (2s, CH2O); 2.29 (s, 2 ortho-CH3); 2.20 (s, para-CH3).

1. temperaturethe reaction mixture was heated
2. temperatureto reflux for one hour
3. temperaturethe reaction was heated
4. temperatureto reflux for another two hours
5. filtrationThe resulting precipitate was collected by filtration
6. dissolutiondissolved into water (60 ml)
7. customwas acidified to pH 2 at 5° C. by 6N HCl
8. customwas then isolated by filtration

ORD record

ord-d40307e150254974b3809d19dc4a7e15

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703821B2