Allyl Alcohol → HCID 86588599, compound

HRID 1826153Notes

Reaction equation

HRID 1826153 reaction equation
[C:1]([C:4]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:7]([O:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[C:6]([O:19][CH3:20])[CH:5]=1)([OH:3])=[O:2].O.[C:22]1(C)[CH:27]=CC(S(O)(=O)=O)=C[CH:23]=1.C(O)C=C>>[C:1]([C:4]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:7]([O:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[C:6]([O:19][CH3:20])[CH:5]=1)([OH:3])=[O:2].[CH3:27][CH:22]=[CH2:23]

Participants

4

Reactant 3

HCID 7858Allyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrateHCID 10684512HCID 10684512, compound

Product 1

HCID 86588599HCID 86588599, compoundYield 795.6%

Procedure

A mixture of 3-(4-carboxy-2-methoxy-5-nitrophenoxy)propanoic acid (153) (20 g, 74.3 mmol) and p-toluene sulphonic acid monohydrate (2.3 g, 7.4 mmol) in allyl alcohol (240 mL, 3.5 mol) was refluxed for 7 hours then allowed to cool. The allyl alcohol was then removed in vacuo, and the residue triturated with dilute HCl acid and collected by filtration. This solid was taken up in EtOAc, and the resulting solution washed with water and brine and dried over sodium sulphate. Evaporation in vacuo afforded 154 as a white solid (19.27 g, 84%): mp 128-130° C.; 1H-NMR (CDCl3): δ 2.92 (t, 2H, J=6.35 Hz); 3.94 (s, 3H); 4.38 (t, 2H, J=6.41 Hz); 4.65 (d, 2H, J=5.61 Hz); 5.27 (dd, 1H, J1=1.28 Hz, J2=19.42 Hz); 5.33 (dd, 1H, J1=1.28 Hz, J=17.04 Hz); 5.92 (m, 1H); 7.15 (s, 1H); 7.45 (s, 1H); 13C NMR (67.8 MHz, CDCl3): δ 34.1, 56.5, 65.0, 65.4, 108.5, 111.3, 118.3, 122.9, 131.8, 141.1, 149.1, 152.6, 167.1, 170.0; IR (Nujol); ν 1730, 1630, 1550, 1430, 1390, 1290, 1230, 1190, 1170, 1070, 1030, 1010 cm−1; MS (EI) m/z (relative intensity): 325 (M+., 19), 251 (3), 213 (2), 196 (3), 211 (3), 113 (19), 91 (4), 71 (9), 55 (6); HRMS: calcd. for C14H15NO6 325.0798, found 232.0773.

Workup

  1. temperaturewas refluxed for 7 hours
  2. temperatureto cool
  3. customThe allyl alcohol was then removed in vacuo
  4. customthe residue triturated with dilute HCl acid
  5. filtrationcollected by filtration
  6. washthe resulting solution washed with water and brine
  7. dry with materialdried over sodium sulphate
  8. customEvaporation in vacuo

Sources & evidence

ORD record
ord-d1d2b3657fef47889371939b018c857f
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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