2-hydroxy-3-(o-tolyloxy)propyl carbamate Property

Melting point:

about 93°; mp 80-84°

Boiling point:

366.75°C (rough estimate)

Density 

1.2102 (rough estimate)

refractive index 

1.5080 (estimate)

Safety

Toxicity

LD50 in mice (mM/kg): 2.77 i.p.; 7.67 orally (Dresel, Slater)

Hazard and Precautionary Statements (GHS)

2-hydroxy-3-(o-tolyloxy)propyl carbamate Chemical Properties,Usage,Production

Originator

Tolseram,Squibb,US,1954

Definition

ChEBI: Mephenesin carbamate is an aromatic ether.

Manufacturing Process

A solution of 32 g (0.30 mol) phosgene in 200 ml benzene is added dropwise at 30°C to a stirred solution of 53.5 g (0.32 mol) 3-o-toloxy-1,2-propanediol in 400 ml benzene. The mixture is stirred for an hour after the addition is completed, and a solution of 39 g of dimethylaniline in 100 ml benzene is then added, and stirring continued for a half-hour. Ice water (about one-third volume) is then added, and the benzene layer formed is separated and stirred with 500 mi concentrated ammonia at 5°C for six hours. The precipitated solid (weighing about 55 g) is recovered and recrystallized from water. The product thus obtained in a yield of about 53 g is 3-(o-toloxy)-2-hydroxypropyl carbamate: it is a crystalline solid melting at about 93°C, and having a lower water-solubility and higher oil-solubility than 3-o-toloxy-1,2-propanediol.

Therapeutic Function

Muscle relaxant

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 3710, 1950 DOI: 10.1021/ja01164a107