Diethyl Ether → Sulisobenzone

HRID 1460856Notes

Reaction equation

HRID 1460856 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Cl[S:19]([OH:22])(=[O:21])=[O:20].CCOCC>C(OC)(=O)C1C(=CC=CC=1)C(OC)=O>[CH3:17][O:16][C:14]1[CH:15]=[C:2]([OH:1])[C:3]([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[CH:12][C:13]=1[S:19]([OH:22])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 46322-Hydroxy-4-methoxybenzophenoneHCID 24638Chlorosulfonic acid

Product 1

HCID 19988Sulisobenzone

Reagents, catalysts & solvents 1

HCID 8554Dimethyl PhthalateSolvent

Procedure

11.4 g of 2-hydroxy-4-methoxybenzophenone were dissolved in 30 ml of dimethyl phthalate at 80° C., and 3.5 ml of chlorosulfonic acid were added dropwise at this temperature. Stirring was carried out for a further 4 hours at 80° C., the mixture was cooled to room temperature and 25 ml of ether were added to the solution. The precipitate was filtered off under suction, washed with ether and hexane and dried under reduced pressure at 30° C. 10 g of 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid of melting point 112°-114° C. were obtained (water content 7.7%).

Workup

  1. filtrationThe precipitate was filtered off under suction
  2. washwashed with ether and hexane
  3. customdried under reduced pressure at 30° C

Sources & evidence

ORD record
ord-fcebcd7a640d4fd183927000023c6b61
Source dataset
uspto-grants-1991_12
Patent number
US05072034

Reaction notes

Loading…