Triethylamine → HCID 53868279, compound

HRID 1862958Notes

Reaction equation

HRID 1862958 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)([O-:15])=[O:14].C(N(CC)CC)C>CN(C)C=O>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][O:11][C:10](=[O:12])[CH2:9][CH2:8][C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 660114-Nitrobenzyl bromide

Product 1

HCID 53868279HCID 53868279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.66 g (10 mmol) of 3-(4-hydroxyphenyl)-propionic acid in 80 ml of dimethylformamide are treated at room temperature and while stirring with 2.16 g (10 mmol) of 4-nitrobenzyl bromide and 1.4 ml (10 mmol) of triethylamine. After 12 hours, the mixture is evaporated in vacuo and the residue obtained partitioned between ethyl acetate and water. The organic phase is separated, washed with 10% potassium hydrogen carbonate solution and water, dried over sodium sulphate and then evaporated to dryness. The residue crystallizes from diisopropyl ether/petroleum ether. There is obtained 3-(4-hydroxyphenyl)-propionic acid 4-nitrobenzyl ester in the form of colourless needles of melting point 80°-82° C. The product is chromatographically pure in cyclohexane/chloroform/acetic acid (45:45:10). The yield amounts to 1.6 g (53% of theory).

Workup

  1. customthe mixture is evaporated in vacuo
  2. customthe residue obtained
  3. custompartitioned between ethyl acetate and water
  4. customThe organic phase is separated
  5. washwashed with 10% potassium hydrogen carbonate solution and water
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness
  8. customThe residue crystallizes from diisopropyl ether/petroleum ether

Sources & evidence

ORD record
ord-85200a1d757d4b60a6df3bc58231cfaa
Source dataset
uspto-grants-1979_09
Patent number
US04167508

Reaction notes

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