Water → HCID 25271922, compound

HRID 1501224Notes

Reaction equation

HRID 1501224 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([O:13]C(C)(C)C)=[O:12])=[CH:9][CH:8]=1)#[N:2].FC(F)(F)C(O)=O.O>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[O:6][C:7]1[CH:19]=[CH:18][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 89581067HCID 89581067, compound

Product 1

HCID 25271922HCID 25271922, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of tert-butyl 4-(3-cyanophenoxy)benzoate (178 mg, 0.6 mmol) in dichloromethane 50 ml) was added trifluoroacetic acid (12.5 ml) the solution was stirred at room temperature for 12 hours, water (50 mL) was added and washed 3 times, the organic layer was evaporated and purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=10:1) to give 4-(3-cyanophenoxy)benzoic acid (40 mg, 28%)

Workup

  1. washwashed 3 times
  2. customthe organic layer was evaporated
  3. custompurified by column chromatography (silica gel, Petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-ded194dbab2940bf9e4e64a52390f8fb
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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