p-Toluenesulfinic acid → P-Anisidine

HRID 53863

Reaction equation

HRID 53863 reaction equation
C1(C)C=CC(S(O)=O)=CC=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19]C(=O)OCC=C)=[CH:15][CH:14]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 10818p-Toluenesulfinic acidHCID 5228341Carbamic acid, 4-methoxyphenyl-, allyl ester

Product 1

HCID 7732P-AnisidineYield 79%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (30.3 mg, 26.2 μmol) was added to a methylene chloride solution (3.7 ml) of p-toluenesulfinic acid (64.3 mg, 0.411 mmol) and allyl N-(p-methoxyphenyl)carbamate (77.6 mg, 0.374 mmol) prepared in Preparation 7. The reaction mixture was stirred for 40 minutes at room temperature. The reaction solution was subjected to a silica gel chromatography to obtain p-anisidine (36.3 mg) with a yield of 79%.

Workup

  1. customprepared in Preparation 7

Sources & evidence

ORD record
ord-43e90eb6e5554891bda41ca849bbe57f
Source dataset
uspto-grants-1997_04
Patent number
US05621084

Linked notes

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