Ethyl 2-(4-(benzyloxy)-2-formylphenoxy)-2-methylpropanoate → Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate

HRID 1785192Notes

Reaction equation

HRID 1785192 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]CC2C=CC=CC=2)=[CH:11][C:10]=1[CH:23]=O)([CH3:7])[CH3:6])[CH3:2].[H][H]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:23])([CH3:6])[CH3:7])[CH3:2]

Participants

5

Reactant 2

HCID 53421768Ethyl 2-(4-(benzyloxy)-2-formylphenoxy)-2-methylpropanoateHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

2-(4-Benzyloxy-2-formyl-phenoxy)-2-methyl-propionic acid ethyl ester (9.00 g, 26.3 mmol) in ethanol (250 mL) is treated with 5% Pd/C (1.25 g) and hydrogen (60 psi, rt, overnight). Additional 5% Pd/C (1.25 g) is added, and the reaction is continued for 6 h at 40° C. The mixture is 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) δ 1.26 (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 is filtered
  2. concentrationconcentrated to a tan oil (6.25 g)

Sources & evidence

ORD record
ord-3004087dba1245818291045ae96c8e20
Source dataset
uspto-grants-2009_03
Patent number
US07504433B2

Reaction notes

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