Potassium Hydroxide → 3-(o-Hydroxymethylphenylthio)-4-hydroxybenzoic acid

HRID 977909Notes

Reaction equation

HRID 977909 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].I[C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[OH:20])[C:14]([OH:16])=[O:15].[OH-].[K+]>O.[Cu]>[OH:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[S:1][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[OH:20])[C:14]([OH:16])=[O:15]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1382782-MercaptobenzenemethanolHCID 4494734-Hydroxy-3-iodobenzoic acid (2IPCOOH)

Product 1

HCID 202039813-(o-Hydroxymethylphenylthio)-4-hydroxybenzoic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 25 gm o-mercaptobenzyl alcohol (0.18 mole), 39.6 gm 3-iodo-4-hydroxy benzoic acid (0.15 mole), 11.43 g copper powder (0.18 mole), 70 cc 40% aqueous potassium hydroxide solution (0.5 mole) and 300 cc water was placed under nitrogen atmosphere and stirred under reflux for 18 hours. After cooling the mixture was diluted with 400 cc of water and extracted twice with 100 cc of ethyl acetate to remove neutral products. The aqueous fraction was filtered and the filtrate acidified with conc. HCl to afford the title compound as an oil which solidified and was filtered. There was obtained 32.8 g of solid product.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling the mixture
  3. extractionextracted twice with 100 cc of ethyl acetate
  4. customto remove neutral products
  5. filtrationThe aqueous fraction was filtered

Sources & evidence

ORD record
ord-507c5bcd714b4166a721701d3270d4d1
Source dataset
uspto-grants-1987_05
Patent number
US04663307

Reaction notes

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