Ammonium Chloride → Methyl 3-chloro-5-(hydroxymethyl)benzoate

HRID 1656476Notes

Reaction equation

HRID 1656476 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:12]=[C:11]([Cl:13])[CH:10]=[C:6]([C:7](O)=[O:8])[CH:5]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:10]=[C:11]([Cl:13])[CH:12]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 247289213-Chloro-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 53712641Methyl 3-chloro-5-(hydroxymethyl)benzoateYield 107%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 3 liter 3-necked round-bottom flask equipped with mechanical stirrer and nitrogen inlet was placed 5-chloroisophthalic acid monomethyl ester (29.4 g). Borane tetrahydrofuran complex in tetrahydrofuran solution (1M, 280 ml) was then added to the flask dropwise at room temperature. The resulting solution was stirred at room temperature overnight. The reaction mixture was poured into saturated aqueous ammonium chloride solution (750 ml) and extracted with ethyl acetate (3×500 ml). The combined organic layers were agitated with 2% aqueous hydrochloric acid, washed with water, dried and the solvent eliminated in the rotavap yielding 29.4 g of 3-chloro-5-hydroxymethyl benzoic acid methyl ester as a clear oil.

Workup

  1. customIn a 3 liter 3-necked round-bottom flask equipped with mechanical stirrer and nitrogen inlet
  2. extractionextracted with ethyl acetate (3×500 ml)
  3. stirringThe combined organic layers were agitated with 2% aqueous hydrochloric acid
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-48dfb1432a1341d8bf07d6725611ace2
Source dataset
uspto-grants-1993_10
Patent number
US05254584

Reaction notes

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