3-(1,3-Dihydroxy-3-m-tolyl-propyl)-4-methoxy-benzoic acid methyl ester → 4-Methoxy-3-(3-m-tolyl-propyl)-benzoic acid methyl ester

HRID 521467Notes

Reaction equation

HRID 521467 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH:12](O)[CH2:13][CH:14](O)[C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[CH:5]=1.[H][H]>C(O)C.Cl.[Pd]>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[CH:5]=1

Participants

6

Reactant 2

HCID 670766153-(1,3-Dihydroxy-3-m-tolyl-propyl)-4-methoxy-benzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 670764524-Methoxy-3-(3-m-tolyl-propyl)-benzoic acid methyl esterYield 63.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

The compound of step 1 (140 mg, 0.424 mmol) was dissolved in ethanol (10 ml) and 12 N hydrochloric acid (0.2 ml), palladium on charcoal (10%) was added, and the mixture was hydrogenated at a hydrogen pressure of 6 bar at room temperature overnight. After filtration and evaporation, the residue was purified by silica gel chromatography (HEP/EA gradient) to give 80 mg of the title compound.

Workup

  1. filtrationAfter filtration and evaporation
  2. customthe residue was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-52b72b9c2fc346e897684b1e723141d9
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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