4-Benzyloxy-2-hydroxybenzaldehyde → 2-(5-Hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester

HRID 1242401Notes

Reaction equation

HRID 1242401 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[CH:12]=[CH:11][C:10]=1[CH:23]=O)([CH3:7])[CH3:6])[CH3:2].C(OC1C=CC(C=O)=C(O)C=1)C1C=CC=CC=1.C(CC(Br)(C)C([O-])=O)C>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[C:5]([O:8][C:9]1[CH:14]=[C:13]([OH:15])[CH:12]=[CH:11][C:10]=1[CH3:23])([CH3:6])[CH3:7])[CH3:2]

Participants

6

Reactant 3

HCID 5612354-Benzyloxy-2-hydroxybenzaldehydeHCID 22490247Ethyl-bromoisobutyrateHCID 86597806HCID 86597806, compound

Product 1

HCID 670724112-(5-Hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl esterYield 94.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5.10 g (14.9 mmol) 2-(5-benzyloxy-2-formyl-phenoxy)-2-methyl-propionic acid ethyl ester (prepared from 4-benzyloxy-2-hydroxybenzaldehyde and ethyl-bromoisobutyrate in analogy to the procedure described in example 52A]) was dissolved in 100 ml of ethanol and hydrogenated with 1.0 g of Pd—C (5%), 2 bar H2, 25° C., for two hours. The reaction mixture was filtered (Celite), the filter cake was washed twice with EtOH and the filtrate was evaporated. The crude product was purified by flash chromatography (SiO2, heptane/EtOAc) to give 3.37 g of the title compound as light yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered (Celite)
  2. washthe filter cake was washed twice with EtOH
  3. customthe filtrate was evaporated
  4. customThe crude product was purified by flash chromatography (SiO2, heptane/EtOAc)

Sources & evidence

ORD record
ord-6b44bb65742246d987a406a3c00b74d2
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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