N,N-Diethylaniline → Methyl 3-allyl-4-hydroxybenzoate

HRID 1511205Notes

Reaction equation

HRID 1511205 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:10]CC=C)=[CH:6][CH:5]=1.C(N(CC)[C:18]1[CH:23]=CC=C[CH:19]=1)C>C(OCC)C>[CH2:23]([C:8]1[CH:9]=[C:4]([CH:5]=[CH:6][C:7]=1[OH:10])[C:3]([O:2][CH3:1])=[O:14])[CH:18]=[CH2:19]

Participants

4

Reactant 2

HCID 7061N,N-DiethylanilineHCID 4645407Methyl 4-(allyloxy)benzoate

Product 1

HCID 939882Methyl 3-allyl-4-hydroxybenzoateYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl-4-allyloxy-benzoate (4.74 g, 24.7 mmol) in N,N-diethylaniline (10 mL) was heated at reflux for 48 hours and cooled to room temperature. The mixture was diluted with diethyl ether (50 mL), washed with aqueous HCl (10% v/v, 3×20 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography (10:1→5:1, hexanes:EtOAc) to afford 5 (3.55 g, 75%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 7.86-7.84 (m, 2H), 6.85 (dd, J=2.8, 7.7 Hz, 1H), 6.07-5.95 (m, 1H), 5.68 (s, 1H), 5.21-5.15 (m, 2H), 3.88 (s, 3H), 3.45 (d, J=6.3 Hz, 2H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. washwashed with aqueous HCl (10% v/v, 3×20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (10:1→5:1, hexanes:EtOAc)

Sources & evidence

ORD record
ord-3da9b45442e243b087427ad160ce31ac
Source dataset
uspto-grants-2012_07
Patent number
US08212011B2

Reaction notes

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