N,N-Dimethylaniline → Ethyl 3-allyl-4-hydroxybenzoate

HRID 256398Notes

Reaction equation

HRID 256398 reaction equation
C([O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1)C=C.CN(C)[C:18]1[CH:23]=CC=C[CH:19]=1>>[CH2:23]([C:15]1[CH:14]=[C:8]([CH:7]=[CH:6][C:5]=1[OH:4])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:18]=[CH2:19]

Participants

3

Reactant 2

HCID 949N,N-DimethylanilineHCID 227685Ethyl 4-(prop-2-en-1-yloxy)benzoate

Product 1

HCID 12252872Ethyl 3-allyl-4-hydroxybenzoate

Procedure

A mixture of 82.3 g (0.899 mole) ethyl 4-allyloxybenzoate in 100 ml N,N-dimethylaniline was stirred under nitrogen while heating at reflux for 2 days. The resulting mixture was cooled to room temperature, the solvent distilled in vacuo, the residue taken up in ethyl ether, washed three times with 1N hydrochloric acid and extracted with 1N sodium hydroxide solution. The alkaline extract was acidified to pH 3.0, extracted with ethyl ether and the extracts dried (MgSO4). Evaporation of solvent provided 47.1 g of the desired product as a solid, TLC with 1.5:1 isopropyl ether/hexane gave one spot, Rf 0.2.

Workup

  1. temperaturewhile heating
  2. temperatureat reflux for 2 days
  3. distillationthe solvent distilled in vacuo
  4. washwashed three times with 1N hydrochloric acid
  5. extractionextracted with 1N sodium hydroxide solution
  6. extractionThe alkaline extract
  7. extractionextracted with ethyl ether
  8. dry with materialthe extracts dried (MgSO4)
  9. customEvaporation of solvent

Sources & evidence

ORD record
ord-af731a8eb1f64edca1b86a4690fa5a62
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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