5-Vinylresorcinol dibenzylether → 5-Ethylbenzene-1,3-diol

HRID 482115Notes

Reaction equation

HRID 482115 reaction equation
[CH:1]([C:3]1[CH:9]=[C:7]([OH:8])[C:6]2C3C(COCC4C([C:4]=1[C:5]=2[OH:25])=CC=CC=4)=CC=CC=3)=[CH2:2]>C(O)C.[Pd]>[CH2:1]([C:3]1[CH:4]=[C:5]([OH:25])[CH:6]=[C:7]([CH:9]=1)[OH:8])[CH3:2]

Participants

4

Reactant 1

HCID 1317207965-Vinylresorcinol dibenzylether

Product 1

HCID 127958985-Ethylbenzene-1,3-diolYield 109.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.07 g (3.39 mmol) of 5-vinylresorcinol dibenzylether, as prepared in the preceding step, and 200 mg of 10% Pd/C in 20 mL of ethanol was hydrogenated at atmospheric pressure and ambient temperature for 14 h. The reaction mixture was filtered through diatomaceous earth (ethanol rinse) and concentrated to give 511 mg of the crude title compound which was used as is in the next reaction. 1H-NMR (300 MHz, CDCl3): δ 6 6.27 (dd, 1H, J=0.4, 2.2 Hz), 6.18 (t, 2H), 2.53 (q, 2H), 1.19 (t, 3H). Mass spectrum (MALDI-TOF; sinapinic acid matrix) calcd. for C8H10O2 :139.1 (M+H). Found: 139.5.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth (ethanol rinse)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7f26860c1048485aa197c18494ff9e6e
Source dataset
uspto-grants-1998_08
Patent number
US05792769

Reaction notes

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