Butyl bromide → 5-(1-Butyloxy)-2-nitrobenzyl alcohol

HRID 862664

Reaction equation

HRID 862664 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7][OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH3:22]>CN(C)C(=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7][OH:8])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 1089463-(Hydroxymethyl)-4-nitrophenol

Product 1

HCID 540218025-(1-Butyloxy)-2-nitrobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
20 °C

Procedure

5.1 g (30 mmol) of 5-hydroxy-2-nitrobenzyl alcohol were stirred with 2.5 g (18 mmol) of potassium carbonate and 25 ml of N,N-dimethylacetamide at 70°-80° C. for 30 minutes. After cooling to 20° C., 3.9 ml (36 mmol) of 1-butylbromide were added dropwise and the mixture was stirred at 90° C. for 2 hours. After cooling, the reaction mixture was concentrated in vacuo, the residue was treated with water and the pH was brought to 7 with 2N HCl. The oil obtained crystallizes after about 30 minutes; the product was filtered off with suction, washed with water and dried; 6 g, melting point 47°-49° C.

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionthe residue was treated with water
  4. customThe oil obtained
  5. customcrystallizes after about 30 minutes
  6. filtrationthe product was filtered off with suction
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-eab0bfe592004e65b31fefd351a48f31
Source dataset
uspto-grants-1998_02
Patent number
US05719164

Linked notes

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