Sulfur Dioxide → Ibuprofen methyl ester

HRID 1906056Notes

Reaction equation

HRID 1906056 reaction equation
CN(C)[CH:3]=[O:4].CO[C:8](OC)([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=1)[CH:9]([OH:11])C.S(=O)=O.ClCl.[CH:29](Cl)(Cl)Cl>>[CH2:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:8]([CH3:29])[C:9]([O:4][CH3:3])=[O:11])=[CH:17][CH:16]=1)[CH:19]([CH3:20])[CH3:21]

Participants

6

Reactant 5

HCID 1119Sulfur DioxideHCID 6212ChloroformHCID 6228DimethylformamideHCID 24526ChlorineHCID 13504793HCID 13504793, compound

Product 1

HCID 109101Ibuprofen methyl ester

Procedure

In this example, 11 g of N,N-dimethylformamide was added to 2.52 g of α-hydroxy-p-isobutylpropiophenone dimethylacetal. Then, 18 ml of sulfur dioxide and 1.1 g of chlorine were added to the mixture at -50° C. The temperature was elevated to 10° C. over 2 hours, and 20 ml of chloroform was added thereto. Subsequent post-treatment was performed in a manner similar to Example 8 to obtain 1.1 g of methyl 2-(4-isobutylphenyl)propionate.

Sources & evidence

ORD record
ord-fadc255fd6ce492b996c25556a1c5e91
Source dataset
uspto-grants-1987_03
Patent number
US04649213

Reaction notes

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