Ammonium Chloride → HCID 15341803, compound

HRID 1756196Notes

Reaction equation

HRID 1756196 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 (4.4g) 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-803769de7ef34d8b84ef2e4ef4c0faff
Source dataset
uspto-grants-1995_08
Patent number
US05439937

Reaction notes

Loading…