Chlorosulfonic acid → HCID 23112079, compound

HRID 1814162Notes

Reaction equation

HRID 1814162 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[Cl:14][S:15](O)(=[O:17])=[O:16]>>[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([S:15]([Cl:14])(=[O:17])=[O:16])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

Product 1

HCID 23112079HCID 23112079, compoundYield 57%

Procedure

Chlorosulfonic acid (10 mL) was cooled to 0° C. Then compound 36A (6.80 g, 38.6 mmol) was added over 30 min. The mixture was stirred at RT for 3 h and was poured into ice (−500 g). The cloudy solution was extracted with ether (2×200 mL). The extracts were dried with magnesium sulfate and concentrated to give a brown oil which was passed through a short pad of silica gel to afford the desired product 36B (6.05 g, 57%) as white plates. MS: 239 (M−Cl)+. Step 3. Preparation of 1-(4-Mercapto-phenyl)cyclopropanecarboxylic acid methyl ester (Compound 36C)

Workup

  1. extractionThe cloudy solution was extracted with ether (2×200 mL)
  2. dry with materialThe extracts were dried with magnesium sulfate
  3. concentrationconcentrated
  4. customto give a brown oil which

Sources & evidence

ORD record
ord-030581c231e747a5820e10db6453436b
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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