Hydrochloric Acid → HCID 118071495, compound

HRID 1775435Notes

Reaction equation

HRID 1775435 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[Cl:14])C=C.C(N(CC)[C:18]1[CH:23]=CC=C[CH:19]=1)C.Cl>>[CH2:23]([C:10]1[CH:9]=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=[C:6]([Cl:14])[C:5]=1[OH:4])[CH:18]=[CH2:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 7061N,N-DiethylanilineHCID 60356835HCID 60356835, compound

Product 1

HCID 118071495HCID 118071495, compound

Conditions

Temperature
210 °C

Procedure

A mixture of 1-(allyloxy)-2-chloro-4-nitrobenzene (55.2 g) and N,N-diethylaniline (50.0 mL) was stirred at 210° C. for 6 hours, and then followed by stirring at 175° C. overnight. At room temperature, the pH of the reaction mixture was adjusted to 1 by the addition of concentrated hydrochloric acid, followed by extraction with ether. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate, the insoluble materials were separated by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 88:12) to obtain 2-allyl-6-chloro-4-nitrophenol (30.1 g) as a yellow solid.

Workup

  1. stirringby stirring at 175° C. overnight
  2. extractionfollowed by extraction with ether
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe insoluble materials were separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 88:12)

Sources & evidence

ORD record
ord-b07e1a4b88324fa3a8d8e2b078d52bc9
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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