N,N-Dimethylaniline → Dimethyl 4-allyl-5-hydroxyisophthalate

HRID 1177359Notes

Reaction equation

HRID 1177359 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([C:15]([O:17][CH3:18])=[O:16])[CH:8]=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11])C=C.CN(C)[C:21]1[CH:26]=CC=C[CH:22]=1>CCOC(C)=O>[CH2:26]([C:14]1[C:5]([OH:4])=[CH:6][C:7]([C:15]([O:17][CH3:18])=[O:16])=[CH:8][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[CH:21]=[CH2:22]

Participants

4

Reactant 2

HCID 949N,N-DimethylanilineHCID 10933919Dimethyl 5-(allyloxy)isophthalate

Product 1

HCID 11791598Dimethyl 4-allyl-5-hydroxyisophthalateYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of dimethyl 5-(allyloxy)isophthalate (1.5 g, 5.994 mmol) in N,N-dimethylaniline (15 mL) was heat at 200° C. for 14 hours. After it was cooled to room temperature, the reaction was diluted with EtOAc, washed with 0.5 N HCl, brine, and dried with Na2SO4. The solvent was evaporated under reduced pressure. The desired product was purified via silica gel gradient column chromatography with EtOAc/Hex (10-25%) to afford the title compound (750 mg, yield 70%) as a white solid. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.82 (d, J=6.22 Hz, 2 H) 3.92 (d, J=5.84 Hz, 6 H) 5.02-5.11 (m, 1 H) 5.10-5.17 (m, 1 H) 5.81 (s, 1 H) 5.90-6.13 (m, 1 H) 7.70 (d, J=1.70 Hz, 1 H) 8.11 (d, J=1.51 Hz, 1 H); LC-MS (ESI)+m/z=251.00 (M+H)+.

Workup

  1. washwashed with 0.5 N HCl, brine
  2. dry with materialdried with Na2SO4
  3. customThe solvent was evaporated under reduced pressure
  4. customThe desired product was purified via silica gel gradient column chromatography with EtOAc/Hex (10-25%)

Sources & evidence

ORD record
ord-a9edea11ba194d60b73cc659e7502eab
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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