HCID 12743495, compound → HCID 18518301, compound

HRID 1108882Notes

Reaction equation

HRID 1108882 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]([OH:19])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOCC>[CH3:15][O:14][C:12]1[CH:11]=[CH:10][C:9]2[CH2:16][C:17](=[O:19])[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[CH2:1][C:8]=2[CH:13]=1

Participants

3

Reactant 1

HCID 12743495HCID 12743495, compound

Product 1

HCID 18518301HCID 18518301, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Finely powdered 2-benzyl-4-methoxyphenylacetic acid (3.26 g, 12.72 mmol) was added to well-stirred polyphosphoric acid (165 g) at 100-110° C. After 15 min, the reaction was poured onto ice (330 g). Et2O (330 mL) was added, and the mixture was stirred briskly for 15 min. The layers were separated, and the aqueous layer was extracted with Et2O (330 mL). The combined organic layers were washed with 5% NaHCO3 (2×80 mL) then with brine (80 mL), dried (MgSO4), and concentrated. The residue was reconcentrated from toluene, then was chromatographed (silica gel, 20% EtOAc/hexarnes). The title compound was obtained as a yellow solid (1.44 g, 48%): TLC Rf (20% EtOAc/hexanes) 0.46; 1H NMR (250 MHz, CDCl3) δ 8.07-8.15 (m, IH), 7.39-7.49 (m, 1H), 7.25-7.48 (m, 2H), 7.19 (d, J=8.3 Hz, 1H), 6.86 (d, J=2.6 Hz, 1H), 6.71 (dd, J=8.3, 2.6 Hz, 1H), 4.21 (s, 2H), 4.11 (s, 2H), 3.77 (s, 3H); FTIR (CCl4) 1680, 1501, 1282, 1270 cm-1 ; MS (ES) m/e 261 (M+Na)+, 256.0 (M+NH4)+, 239.0 (M+H)+.

Workup

  1. additionthe reaction was poured onto ice (330 g)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with Et2O (330 mL)
  4. washThe combined organic layers were washed with 5% NaHCO3 (2×80 mL)
  5. dry with materialwith brine (80 mL), dried (MgSO4)
  6. concentrationconcentrated
  7. customwas chromatographed (silica gel, 20% EtOAc/hexarnes)

Sources & evidence

ORD record
ord-570ba72b102b454d8e759d3b5003fc21
Source dataset
uspto-grants-2000_05
Patent number
US06069158

Reaction notes

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