Ammonium Chloride → HCID 15341803, compound

HRID 893453Notes

Reaction equation

HRID 893453 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH:13]=[CH2:14])=[C:10]([OH:15])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[Cl-].[NH4+:17]>C(O)C>[OH:1][C:2]1[C:11]([CH2:12][CH:13]=[CH2:14])=[C:10]([OH:15])[CH:9]=[CH:8][C:3]=1[C:4]([NH2:17])=[O:5]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 13019279Methyl 2,4-dihydroxy-3-(prop-2-en-1-yl)benzoate

Product 1

HCID 15341803HCID 15341803, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2,4-dihydroxy-3-(2-propenyl)benzoate (4.4 g) was added to a mixture of about 10 to 15 ml of saturated ammonium chloride solution and 2 to 3 ml of ethanol. The reaction mixture was stirred overnight at 50° C. The reaction mixture was extracted five times with ethyl acetate, and the organic layer was concentrated under vacuum. The product was crystallized and recrystallized from chloroform. Subsequent chromatography of the precipitated product on a 25 g silica gel column with 40% ethyl acetate/hexane as eluant gave the pure product.

Workup

  1. extractionThe reaction mixture was extracted five times with ethyl acetate
  2. concentrationthe organic layer was concentrated under vacuum
  3. customThe product was crystallized
  4. customrecrystallized from chloroform
  5. customSubsequent chromatography of the precipitated product on a 25 g silica gel column with 40% ethyl acetate/hexane as eluant gave the pure product

Sources & evidence

ORD record
ord-b34b2ae59d3848c7b2f3540be1d3827b
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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