Triethylamine → HCID 58427514, compound

HRID 2065432Notes

Reaction equation

HRID 2065432 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.C(N(CC)CC)C.Cl[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>CC(C)=O>[C:25]([O:24][C:22]([CH2:21][O:11][C:10](=[O:12])[CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103943-(4-Hydroxyphenyl)propionic acidHCID 66052tert-Butyl chloroacetate

Product 1

HCID 58427514HCID 58427514, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 3-(4-hydroxy phenyl) propionic acid (20 grams, 120.35 mmol) and triethyl amine (30 grams, 296.47 mmol) in acetone (150 mL) is added t-butyl chloroacetate (19.6 grams, 130 mmol) drop wise, later it is stirred under reflux for 10 hours. The resulting solids are filtered off, acetone is distilled off, and water (100 mL) is added. The crude 4 is extracted into chloroform, and is washed with 5% sodium bicarbonate (2×25 mL), water (2×25 mL), and the product is dried over sodium sulphate, and is distilled to give crude 4 which can be purified from an appropriate solvent.

Workup

  1. temperatureunder reflux for 10 hours
  2. filtrationThe resulting solids are filtered off
  3. distillationacetone is distilled off
  4. additionwater (100 mL) is added
  5. extractionThe crude 4 is extracted into chloroform
  6. washis washed with 5% sodium bicarbonate (2×25 mL), water (2×25 mL)
  7. dry with materialthe product is dried over sodium sulphate
  8. distillationis distilled
  9. customto give crude 4 which
  10. customcan be purified from an appropriate solvent

Sources & evidence

ORD record
ord-802a2b3af6d34282a93b82df81b81d51
Source dataset
uspto-grants-2012_10
Patent number
US08288505B2

Reaction notes

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