Chlorosulfonic acid → 2-(4-Chlorosulfonyl-3-methoxy-phenyl)-2-methyl-propionic acid methyl ester

HRID 1814160Notes

Reaction equation

HRID 1814160 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][O:7][C:8](=[O:20])[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)([CH3:11])[CH3:10]>>[CH3:6][O:7][C:8](=[O:20])[C:9]([C:12]1[CH:17]=[CH:16][C:15]([S:2]([Cl:1])(=[O:5])=[O:3])=[C:14]([O:18][CH3:19])[CH:13]=1)([CH3:11])[CH3:10]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 21883537Methyl 2-(3-methoxyphenyl)-2-methylpropanoate

Product 1

HCID 207708262-(4-Chlorosulfonyl-3-methoxy-phenyl)-2-methyl-propionic acid methyl esterYield 36%

Procedure

Chlorosulfonic acid (11.5 mL) was cooled to 0° C. Then compound 21A (4.6 g, 22 mmol) was added over 15 min. The mixture was stirred at RT for 3 h and then poured into ice (100 g). The cloudy solution was extracted with CH2Cl2 (2×50 mL) The extracts were dried with MgSO4 and concentrated to give a purple oil which was passed through a short pad of silica gel to afford the desired product 21B (2.43 g 36%) as an orange oil. MS m/z 271 (M−Cl). Step 3. Preparation of 2-(4-Mercapto-3-methoxy-phenyl)-2-methyl propionic acid methyl ester (Compound 21C)

Workup

  1. extractionThe cloudy solution was extracted with CH2Cl2 (2×50 mL) The extracts
  2. dry with materialwere dried with MgSO4
  3. concentrationconcentrated
  4. customto give a purple oil which

Sources & evidence

ORD record
ord-af13c468020a4a918df3080d294bd641
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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