Sulfuric Acid → 2,5-Dimethyl-4-mercaptophenoxy-acetic acid ethyl ester

HRID 549562Notes

Reaction equation

HRID 549562 reaction equation
COC(=O)C.[CH2:6]([O:8][C:9](=[O:24])[CH2:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([S:19](Cl)(=O)=O)=[CH:14][C:13]=1[CH3:23])[CH3:7].S(=O)(=O)(O)O>C(O)C>[CH2:6]([O:8][C:9](=[O:24])[CH2:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([SH:19])=[CH:14][C:13]=1[CH3:23])[CH3:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6584Methyl Acetate2×HCID 20768123Ethyl [4-(chlorosulfonyl)-2,5-dimethylphenoxy]acetate

Product 1

HCID 207681072,5-Dimethyl-4-mercaptophenoxy-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(4-Mercapto-2,5-dimethyl-phenoxy)-acetic acid ethyl ester was prepared as described for 2,6-difluoro-4-mercapto-phenoxy)acetic acid methyl ester (compound 21) in Eur. J. Med. Chem., 1995, 30, 403 (Kawashima, M. S.) except that (4-chlorosulfonyl-2,5-dimethylphenoxy)-acetic acid ethyl ester was reduced with 4 eq. of zn (dust) in a mixture of konc. sulfuric acid and ethanol at 80° C.

Workup

  1. customat 80° C.

Sources & evidence

ORD record
ord-4ef7f8a28c2a4673bf0ed81d2f4f2c08
Source dataset
uspto-grants-2011_05
Patent number
US07943669B2

Reaction notes

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