Ethyl 2-(4-(benzyloxy)-2-formylphenoxy)-2-methylpropanoate → 2-(4-Hydroxy-2-hydroxymethylphenoxy)-2-methylpropionic acid ethyl ester

HRID 1181136Notes

Reaction equation

HRID 1181136 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:24])([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[CH2:23][OH:24])([CH3:7])[CH3:6])[CH3:2]

Participants

5

Reactant 2

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

Product 1

HCID 235900102-(4-Hydroxy-2-hydroxymethylphenoxy)-2-methylpropionic acid ethyl esterYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Benzyloxy-2-formyl-phenoxy)-2-methyl-propionic acid ethyl ester (185 g, 540 mmol) in ethanol (700 mL) was treated with 10% Pd/C (205 g) and hydrogen (60 psi) at 50° C. for 2 d. The mixture was filtered through Celite, washed with ethanol (1.5 L), and concentrated. The residue was recrystallized from EtOAc/hexanes to give the title compound (116 g). 1H NMR (400 MHz, CDCl3) δ 1.26 (t, 3H, J=7.3 Hz), 1.52 (s, 6H), 2.14 (s, 3H), 4.23 (q, 2H, J=7.3 Hz), 4.59 (brs, 2H), 6.61-6.68 (m, 2H), 6.77 (d, 1H, J=2.8 Hz).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with ethanol (1.5 L)
  3. concentrationconcentrated
  4. customThe residue was recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-775d1cd476cf494db460cff21a98fa43
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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