4-tert-Butylphenol → HCID 18661300, compound

HRID 965231Notes

Reaction equation

HRID 965231 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:10]2[CH2:11][C:12]3[C:17]([CH:9]12)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([O:28][C@@H:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@@H:10]2[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:26][CH:27]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 73934-tert-ButylphenolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 53697243(+/-)N-tert-butoxycarbonyl-1,2-iminoindane

Product 1

HCID 18661300HCID 18661300, compoundYield 16.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of (±) N-tert-butoxycarbonyl-1,2-iminoindane (5 g, 22 mmol), 4-tert-butylphenol (3.34 g, 22 mmol) and pyridinium p-toluenesulfonate (109 mg) in chloroform (150 ml) was heated at reflux for 2 h. On cooling, the solution was washed sequentially with 10% aq. NaOH, water and then brine. After drying over MgSO4, solvents were removed in vacuo and the resultant brown oil subjected to column chromatography on silica gel eluting with 20% diethyl ether in hexanes to afford the title compound (1.42 g).

Workup

  1. temperatureat reflux for 2 h
  2. temperatureOn cooling
  3. washthe solution was washed sequentially with 10% aq. NaOH, water
  4. dry with materialAfter drying over MgSO4, solvents
  5. customwere removed in vacuo

Sources & evidence

ORD record
ord-6000a3684d8d43fc96327fc7a4aa1833
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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