Trichloroisocyanuric Acid → 3-(3-Chloro-4-hydroxy-phenyl)-propionic acid benzyl ester

HRID 2170112Notes

Reaction equation

HRID 2170112 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20]N1C(=O)N(Cl)C(=O)N(Cl)C1=O>CC#N.O>[CH2:1]([O:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([OH:18])=[C:16]([Cl:20])[CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 14211262Benzyl 3-(4-hydroxyphenyl)propanoate

Product 1

HCID 667975723-(3-Chloro-4-hydroxy-phenyl)-propionic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(4-hydroxy-phenyl)-propionic acid benzyl ester (13.36 g, 52.1 mmol) in MeCN (100 ml) was cooled to 0° C. Trichloroisocyanuric acid (4.00 g, 17.2 mmol) was added, and the resulting white suspension was gradually allowed to warm to RT and stirred overnight. The reaction mixture was diluted with water (200 ml) and the product was extracted into EtOAc (250 ml) and dried (MgSO4). Purification by chromatography on silica eluting with 0-20% EtOAc in iso-hexane afforded the title product; 1H NMR (400 MHz, DMSO-d6) δ 9.90 (1H, s), 7.32 (3H, m), 7.29 (2H, d), 7.18 (1H, d), 6.97 (1H, dd), 6.85 (1H, d), 5.07 (2H, s), 2.76 (2H, t), 2.64 (2H, t). LC-MS Rt 1.46 mins; 313.2 [M+H]+, Method 2minLC_v002.

Workup

  1. extractionthe product was extracted into EtOAc (250 ml)
  2. dry with materialdried (MgSO4)
  3. customPurification by chromatography on silica eluting with 0-20% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-da88751a5d954d7abeea8dff7c49812d
Source dataset
uspto-grants-2015_06
Patent number
US09050339B2

Reaction notes

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