Water → 4-{2-[4-(2-Benzoxazolyl)phenoxy]ethoxy}-2,2,6,6-tetramethylpiperidine

HRID 1448697Notes

Reaction equation

HRID 1448697 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.Br[CH2:19][CH2:20][O:21][CH:22]1[CH2:27][C:26]([CH3:29])([CH3:28])[NH:25][C:24]([CH3:31])([CH3:30])[CH2:23]1.O>C(O)C>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:6]1[CH:5]=[CH:4][C:3]([O:2][CH2:19][CH2:20][O:21][CH:22]2[CH2:23][C:24]([CH3:31])([CH3:30])[NH:25][C:26]([CH3:28])([CH3:29])[CH2:27]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27855874-(Benzo[d]oxazol-2-yl)phenolHCID 5360545SodiumHCID 203752634-(2-Bromoethoxy)-2,2,6,6-tetramethylpiperidine

Product 1

HCID 203752624-{2-[4-(2-Benzoxazolyl)phenoxy]ethoxy}-2,2,6,6-tetramethylpiperidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Equal molar quantities of p-hydroxybenzaldehyde and o-aminophenol in excess nitrobenzene was refluxed for five hours. The nitrobenzene was removed and the residue was washed with hot xylene. 2-(4-Hydroxyphenyl)benzoxazole was obtained by crystallization from ethanol in 64% yield (m.p. 253°). A mixture of the sodium salt of 2-(4-hydroxyphenyl)benzoxazole (0.01 mole) and 4-(2-bromoethoxy)-2,2,6,6-tetramethylpiperidine (0.01 mole) in 250 ml of ethanol was refluxed for 20 hours. The reaction mixture was cooled, 200 ml. of water was added and the product, I, was filtered out.

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe product, I, was filtered out

Sources & evidence

ORD record
ord-507b1b3152f04016ac05e2d4ec0f0c98
Source dataset
uspto-grants-1980_02
Patent number
US04187213

Reaction notes

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