HCID 57845371, compound → HCID 19010673, compound

HRID 734413Notes

Reaction equation

HRID 734413 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[OH:20])[C:7]([O:9]CC1C=CC=CC=1)=[O:8])[CH:2]=[CH2:3]>[Pd].C(O)C>[OH:20][C:19]1[CH:18]=[CH:17][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[CH2:1][CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 57845371HCID 57845371, compound

Product 1

HCID 19010673HCID 19010673, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of benzyl 3-allyl-4-hydroxybenzoate (15.40 g, 57.4 mmol) (Example 41), 10% Pd/C (1.54 g), and 60 mL ethanol was placed in a Parr hydrogenator under 60 psi of H2. The mixture was shaken for 2 h. The catalyst was removed by filtering through a plug of Celite®. The filtrate was concentrated to yield a thick oil (10.5 g 100%). 1H NMR (400 MHz, DMSO-d6) δ 12.36 (br s, 1H), 10.08 (s, 1H), 7.59-7.63 (m, 2H), 6.81 (d, 1H), 2.49-2.53 (m, 2H), 1.50-1.59 (m, 2H), 0.89 (t, 3H).

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through a plug of Celite®
  3. concentrationThe filtrate was concentrated
  4. customto yield a thick oil (10.5 g 100%)

Sources & evidence

ORD record
ord-f6109c1f371246d8b07f6a64283c727c
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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