Trichloroisocyanuric Acid → tert-Butyl 4'-(3-oxopropyl)biphenyl-2-carboxylate

HRID 1927643Notes

Reaction equation

HRID 1927643 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>C(Cl)Cl.CCOCC>[O:1]=[CH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 6909Trichloroisocyanuric AcidHCID 68672795Tert-butyl 4'-(3-hydroxypropyl)biphenyl-2-carboxylate

Product 1

HCID 11722927tert-Butyl 4'-(3-oxopropyl)biphenyl-2-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4′-(3-hydroxypropyl)biphenyl-2-carboxylate (7.00 g, 22.4 mmol) in CH2Cl2 (200 mL) at 0° C. was added trichloroisocyanuric acid (5.47 g, 23.5 mmol) and 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (35 mg, 0.224 mmol). After stirring at it for 20 min, the reaction mixture was diluted with Et2O (200 mL) and filtered through a silica gel pad, rinsing with Et2O (400 mL). The filtrate was concentrated, and the residue was purified by silica gel column chromatography (5-75% EtOAc in Hexanes) to afford the title compound.

Workup

  1. filtrationfiltered through a silica gel pad
  2. washrinsing with Et2O (400 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel column chromatography (5-75% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-b6c16cdb4ce6445196d0ce5764d72edc
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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