3,5-Bis(decyloxy)phenylcarbamic acid phenylmethyl ester → 3,5-Bis(decyloxy)benzeneamine

HRID 1757775Notes

Reaction equation

HRID 1757775 reaction equation
C1(COC(=O)[NH:10][C:11]2[CH:16]=[C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:14]=[C:13]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:12]=2)C=CC=CC=1>[Pd].C(OCC)(=O)C>[CH2:18]([O:17][C:15]1[CH:16]=[C:11]([NH2:10])[CH:12]=[C:13]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH:14]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

4

Reactant 1

HCID 99847623,5-Bis(decyloxy)phenylcarbamic acid phenylmethyl ester

Product 1

HCID 103412613,5-Bis(decyloxy)benzeneamineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 34 g (0.063 mol) of 3,5-bis(decyloxy)phenylcarbamic acid phenylmethyl ester and 4.0 g of 10% palladium on charcoal in 650 ml of ethyl acetate was shaken under a hydrogen atmosphere at room temperature for 4 hours. The reaction mixture was filtered to remove the catalyst and the filtrate was concentrated under reduced pressure to yield 25 g (98% yield, mp 48°-50°) of 3,5-bis(decyloxy)benzenamine.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fda159f160a840258578d9eb8d321755
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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