4-Hydroxybenzoic Acid → 4-hydroxy-N,N-bis(propan-2-yl)benzamide

HRID 2209734Notes

Reaction equation

HRID 2209734 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[CH:22]([NH:25][CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23]>ClCCl>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:25]([CH:26]([CH3:28])[CH3:27])[CH:22]([CH3:24])[CH3:23])=[O:8])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 1354-Hydroxybenzoic AcidHCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 65578Oxalyl chloride

Product 1

HCID 218414724-hydroxy-N,N-bis(propan-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-hydroxybenzoic acid (5 g, 36.2 mmol) in 50 mL of dichloromethane is treated at 0° C. with oxalyl chloride (6.3 mL, 72.4 mmol) and N,N-dimethylformamide (5.6 mL, 72.4 mmol). This solution is stirred at room temperature for 2 hours and treated with diisopropylamine (40 mL, 286 mmol) at 0° C. After stirring at room temperature for overnight, the reaction is partitioned between ethyl acetate and 1N hydrochloride solution. The organic phase is washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford 4-hydroxy-N,N-bis(1-methylethyl)benzamide.

Workup

  1. stirringAfter stirring at room temperature for overnight
  2. customthe reaction is partitioned between ethyl acetate and 1N hydrochloride solution
  3. washThe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89a501b123b5427da8d5d4254818dca5
Source dataset
uspto-grants-1995_10
Patent number
US05455274

Reaction notes

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