Ethanol → Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate

HRID 398142Notes

Reaction equation

HRID 398142 reaction equation
[CH3:1][C:2]([O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14]CCC2N=C(C3C=CC=CC=3)OC=2C)=[CH:10][C:9]=1[CH3:29])([CH3:6])[C:3]([OH:5])=[O:4].[H][H].[CH2:32](O)[CH3:33]>[Pd]>[CH2:32]([O:5][C:3](=[O:4])[C:2]([O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[CH3:29])([CH3:1])[CH3:6])[CH3:33]

Participants

5

Reactant 3

HCID 702EthanolHCID 222611152-Methyl-2-[2-methyl-4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenoxy]propanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

2-Methyl-2-{2-methyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy}propionic acid (9.00 g, 26.3 mmol) in ethanol (250 mL) was treated with 5% Pd/C (1.25 g) and hydrogen (60 psi, room temperature, overnight). Additional 5% Pd/C (1.25 g) was added, and the reaction was continued for 6 h at 40° C. The mixture was filtered and concentrated to a tan oil (6.25 g). This oil contained 9 mol % of 2-(4-Hydroxy-2-hydroxymethyl-phenoxy)-2-methyl-propionic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ1.26 (t, 3H, J=7.3 Hz), 1.51 (s, 6H), 2.14 (s, 3H), 4.24 (q, 2H, J=7.3 Hz), 5.68 (brs, 1H), 6.47 (dd, 1H, J=3.4, 8.8 Hz), 6.59 (d, 1H, J=8.3 Hz), 6.60 (brs, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated to a tan oil (6.25 g)

Sources & evidence

ORD record
ord-b16edb621bd84cffa1826f993fb8b9a6
Source dataset
uspto-grants-2003_08
Patent number
US06610696B2

Reaction notes

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