Water → 3-(o-Carboxyphenylthio)-4-hydroxybenzaldehyde

HRID 977907Notes

Reaction equation

HRID 977907 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20]C)[CH:15]=[O:16])([O:3]C)=[O:2].O>C(O)(=O)C.Br>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[OH:20])[CH:15]=[O:16])([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 962WaterHCID 133386853-(o-Carbomethoxypheylthio-)4-methoxybenzaldehyde

Product 1

HCID 133386863-(o-Carboxyphenylthio)-4-hydroxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

Heat 126 gm of the aldehyde of Step C in a mixture of 1500 cc of glacial acetic acid and 1500 cc of 48% hydrogen bromide in an oil bath at 150° C. with mechanical stirring until no trace of non-demethylated product remains (4-5 days). Cool the reaction mixture and pour into 7 l. of water. Separate the precipitate, wash well with water and dry in vacuo at 70° C. to constant weight. The material is used in the following step without further purification.

Workup

  1. custom(4-5 days)
  2. temperatureCool the reaction mixture
  3. additionpour into 7 l
  4. customSeparate the precipitate
  5. washwash well with water
  6. customdry in vacuo at 70° C. to constant weight
  7. customThe material is used in the following step without further purification

Sources & evidence

ORD record
ord-67e0ea53b5534a80bc1cffdeb07140b7
Source dataset
uspto-grants-1987_05
Patent number
US04663307

Reaction notes

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