3-Hydroxyacetanilide → HCID 725681, compound

HRID 2395032Notes

Reaction equation

HRID 2395032 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][CH:10]=1)C=C.[CH2:15](OC1C=C(C=CC=1)CCl)[CH:16]=[CH2:17].OC1C=C(NC(=O)C)C=CC=1>O(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC>[CH2:17]([C:10]1[CH:9]=[CH:8][C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:6][C:5]=1[OH:4])[CH:16]=[CH2:15]

Participants

6

Reactant 3

HCID 121243-HydroxyacetanilideHCID 258024N-{3-[(Prop-2-en-1-yl)oxy]phenyl}ethanimidic acidHCID 141693671-(Chloromethyl)-3-(2-propen-1-yloxy)benzene

Product 1

HCID 725681HCID 725681, compound

Reagents, catalysts & solvents 2

HCID 7583Diphenyl EtherSolventHCID 8058HexaneSolvent

Procedure

A mixture of N-(3-allyloxyphenyl)acetamide (13.2 g) prepared by a similar method to that of Example 2, Footnote c (A), from N-(3-hydroxyphenyl)acetamide, in Ph2O (100 ml) was heated at 250° C. for 10 minutes, cooled and diluted with hexane (100 ml) to give crystals. The crystals were re-crystallised from ethyl acetate. The liquors were evaporated and dissolved in 0.2M aqueous NaOH, filtered though Celite, and acidified with 1M aqueous HCl solution to give N-(4-allyl-3- hydroxyphenyl)acetamide (3.6 g) mpt. 164°-165° C.

Workup

  1. temperaturecooled
  2. customto give crystals
  3. customThe crystals were re-crystallised from ethyl acetate
  4. customThe liquors were evaporated
  5. dissolutiondissolved in 0.2M aqueous NaOH
  6. filtrationfiltered though Celite

Sources & evidence

ORD record
ord-79c6bde1473548689f8d46caafbc8181
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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