Water → 4-Methoxy-3-sulfanylbenzoic acid

HRID 356940Notes

Reaction equation

HRID 356940 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9])(=O)=O.O>C(O)(=O)C.Cl>[SH:2][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 962WaterHCID 38548883-(Chlorosulfonyl)-4-methoxybenzoic acid

Product 1

HCID 124257504-Methoxy-3-sulfanylbenzoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of 3-chlorosulfonyl-4-methoxybenzoic acid (58 g; that is prepared as described in Reference Example 44) in glacial acetic acid (250 mL) at 40° C. is treated during 15 minutes with a solution of stannous chloride (107 g) in concentrated hydrochloric acid. The mixture is heated at reflux for 2 hours and the hot mixture is then poured into water (2 L) with vigorous stirring. The resulting solid is filtered off and dried, to give crude 3-mercapto-4-methoxybenzoic acid (34 g).

Workup

  1. customthat is prepared
  2. customat 40° C.
  3. temperatureThe mixture is heated
  4. temperatureat reflux for 2 hours
  5. filtrationThe resulting solid is filtered off
  6. customdried

Sources & evidence

ORD record
ord-e9030ee163e34b7c89d025e9741baf45
Source dataset
uspto-grants-1998_11
Patent number
US05840724

Reaction notes

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