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

HRID 1603896Notes

Reaction equation

HRID 1603896 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>C(OCC)(=O)C>[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

4

Reactant 2

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

Product 1

HCID 12252872Ethyl 3-allyl-4-hydroxybenzoateYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
200 °C

Procedure

A mixture of ethyl 4-allyloxybenzoate (10.0 g, 48.5 mmol) and N,N-dimethylaniline (20 ml) was left under stirring at 200° C. for 48 h, then diluted with ethyl acetate (150 ml) and washed with 1M HCl. After drying and evaporating off the solvent, a crude was obtained which was purified by chromatography through a silica gel column, eluting with n-hexane:ethyl acetate, 95:5, thereby recovering 6.85 g of the title compound (69% yield).

Workup

  1. waitwas left
  2. washwashed with 1M HCl
  3. customAfter drying
  4. customevaporating off the solvent
  5. customa crude was obtained which
  6. customwas purified by chromatography through a silica gel column
  7. washeluting with n-hexane

Sources & evidence

ORD record
ord-a205b2b806b34e05a277a32fcf927b65
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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