Water → HCID 18624471, compound

HRID 1861562Notes

Reaction equation

HRID 1861562 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].O.[I:19]Cl.C1(C)C=CC=CC=1>Cl>[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[C:15]([I:19])[CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 24640Iodine chlorideHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate2×

Product 1

HCID 18624471HCID 18624471, compoundYield 98.13%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To stirred solution of racemic ethyl 2-ethoxy-3-(4-hydroxyphenyl)propionate of the formula (13a) (20 g) obtained according to the procedure described in step (v) above and dimineralised water (100 ml), ICl (13.6 g, 4.4 ml) in HCl (80 ml) was added dropwise at room temperature for 30 min. The reaction mixture was heated to 75° C. to 80° C. for 20 h. The progress of the reaction was monitored by TLC. After completion of the reaction, toluene (200 ml) was added to the reaction mixture and extracted with dimineralised water. Organic extracts were concentrated to yield the crude compound. The crude compound was purified by column chromatography using 3% ethyl acetate in pet. ether to yield the title compound (10.3 g, 98.13%)

Workup

  1. customobtained
  2. additionwas added dropwise at room temperature for 30 min
  3. temperatureThe reaction mixture was heated to 75° C. to 80° C. for 20 h
  4. additionwas added to the reaction mixture
  5. extractionextracted with dimineralised water
  6. concentrationOrganic extracts were concentrated
  7. customto yield the crude compound
  8. customThe crude compound was purified by column chromatography

Sources & evidence

ORD record
ord-9d410289240247718b349103c773b1d6
Source dataset
uspto-grants-2003_03
Patent number
US06531596B1

Reaction notes

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