Toluene → HCID 20213855, compound

HRID 1906055Notes

Reaction equation

CO[C:3](OC)([C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14](=[O:16])[CH3:15])=[CH:9][CH:8]=1)[CH:4]([OH:6])C.CN(C)[CH:21]=[O:22].S(Cl)(Cl)(=O)=O.[C:29]1(C)C=CC=CC=1>>[C:14]([O:13][C:10]1[CH:9]=[CH:8][C:7]([CH:3]([CH3:29])[C:4]([O:22][CH3:21])=[O:6])=[CH:12][CH:11]=1)(=[O:16])[CH3:15]

Participants

Reactant 4

HCID 1140Toluene

HCID 6228Dimethylformamide

HCID 24648Sulfuryl chloride

HCID 20213856HCID 20213856, compound

Product 1

HCID 20213855HCID 20213855, compoundYield 80%

Conditions

Temperature: -50 °C

Procedure

In this example, 2.54 g of α-hydroxy-p-acetoxypropiophenone dimethylacetal was dissolved in a mixed solvent of 2 ml of N,N-dimethylformamide and 20 ml of toluene and the solution was cooled to -50° C. Then, 1.75 ml of sulfuryl chloride was added thereto. The mixture was stirred at the same temperature for 3 hours. After completion of the reaction, post-treatment was performed in a manner similar to Example 1 to obtain 1.78 g of methyl 2-(p-acetoxyphenyl)propionate (yield 80%). The product was heated in 20 ml of an aqueous 1N sodium hydroxide solution at 50° C. for 1 hour. Thereafter, the pH was adjusted to 3 with conc. hydrochloric acid. The solution was extracted with 50 ml of chloroform. The extract was concentrated under reduced pressure to obtain 1.2 g of 2-(p-hydroxyphenyl)propionic acid (yield 90%).

Workup

customAfter completion of the reaction

Sources & evidence

ORD record: ord-14a8770c7bf146eb8be6e454739879b2
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04649213

Reaction notes

Loading…