Triethylamine → HCID 58427514, compound

HRID 2090575Notes

Reaction equation

HRID 2090575 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-d38c048c205545aaae69ebb03741ba2c
Source dataset
uspto-grants-2013_05
Patent number
US08436201B2

Reaction notes

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