4-Hydroxybenzaldehyde → HCID 21680068, compound

HRID 1663605Notes

Reaction equation

HRID 1663605 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:15])[C:12](Cl)=[O:13].Cl.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:10][N:11]([CH3:15])[C:12](=[O:13])[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl ChlorideHCID 8857Ethyl Acetate

Product 1

HCID 21680068HCID 21680068, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-hydroxybenzaldehyde (1.22 g) in pyridine (5 mL) was added dimethylcarbamyl chloride (1.0 mL) and the mixture was stirred at 60° C. overnight. Thereto was added diluted HCl and ethyl acetate and stirred. The organic layer was extracted by diatomaceous earth column. The organic layer was concentrated and the resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=80:20→60:40) to give 4-formylphenyl dimethylcarbamate (1.67 g, yield: 86%).

Workup

  1. stirringstirred
  2. extractionThe organic layer was extracted by diatomaceous earth column
  3. concentrationThe organic layer was concentrated
  4. customthe resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=80:20→60:40)

Sources & evidence

ORD record
ord-d512548818af4997ab8165297869e77a
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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