1-(3,4-Bis-benzyloxy-phenyl)-cyclopropanecarbonitrile → 1-(3,4-Dihydroxyphenyl)cyclopropanecarbonitrile

HRID 1908318Notes

Reaction equation

HRID 1908318 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:23]2([C:26]#[N:27])[CH2:25][CH2:24]2)[CH:12]=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([C:23]2([C:26]#[N:27])[CH2:24][CH2:25]2)[CH:12]=[CH:13][C:14]=1[OH:15]

Participants

4

Reactant 1

HCID 670439871-(3,4-Bis-benzyloxy-phenyl)-cyclopropanecarbonitrile

Product 1

HCID 670436561-(3,4-Dihydroxyphenyl)cyclopropanecarbonitrileYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(3,4-bis-benzyloxy-phenyl)-cyclopropanecarbonitrile (10 g, 28 mmol) in MeOH (50 mL) was added Pd/C (0.5 g) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature for 4 h. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum to give 1-(3,4-dihydroxy-phenyl)-cyclopropanecarbonitrile (4.5 g, 92%). 1H NMR (DMSO 400 MHz) δ 9.06 (br s, 2H), 6.67-6.71 (m, 2H), 6.54 (dd, J=2.4, 8.4 Hz, 1H), 1.60-1.57 (m, 2H), 1.30-1.27 (m, 2H).

Workup

  1. filtrationThe catalyst was filtered off through a celite pad
  2. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-8b9495f831c342cfaf0e5c4c9b7a371f
Source dataset
uspto-grants-2013_12
Patent number
US08598181B2

Reaction notes

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