4-Hydroxybenzaldehyde → tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate

HRID 1595496Notes

Reaction equation

HRID 1595496 reaction equation
[N+](C1C=C(S([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:18][CH:17]=2)(=O)=O)C=CC=1)([O-])=O.O[C:31]1[CH:38]=[CH:37][C:34]([CH:35]=[O:36])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:35]([C:34]1[CH:37]=[CH:38][C:31]([O:13][CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:24])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[CH:20][CH:21]=2)=[CH:32][CH:33]=1)=[O:36]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 545354424-(Tert-butoxycarbonylamino)phenethyl 3-nitro-benzenesulfonate

Product 1

HCID 21704970tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

26.7 g (63 mmole) 4-(tert-butoxycarbonylamino)phenethyl 3-nitro-benzenesulfonate, 8.5 g (69 mmole) p-hydroxybenzaldehyde, 9.54 g (69 mmole) potassium carbonate and acetonitrile was refluxed for 3 hours and thereafter stirred over night at room temperature. The precipitate was filtered off and the solvent was evaporated. Dichloromethane was added and the organic phase was washed with saturated sodium carbonate and thereafter with sodium hydroxide (0.1 M), dried (sodium sulfate), filtered and the solvent was evaporated to give 17 g (yield 79%) of tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe solvent was evaporated
  3. additionDichloromethane was added
  4. washthe organic phase was washed with saturated sodium carbonate
  5. dry with materialwith sodium hydroxide (0.1 M), dried (sodium sulfate)
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-00b9dcc3c5b844d1ac6c58706fa40799
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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