Sodium Hydroxide → HCID 86661511, compound

HRID 2410502Notes

Reaction equation

HRID 2410502 reaction equation
[OH-].[Na+].Br[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[OH:12][CH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([CH2:13][O:12][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])=[CH:15][CH:16]=1)#[N:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 160549p-Cyanobenzyl alcohol

Product 1

HCID 86661511HCID 86661511, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

An aqueous solution of NaOH (30 g in 60 mL of water) and tert-butyl bromoacetate (3.75 mL, 25.2 mmol) were added into a solution of 4-(hydroxymethyl)benzonitrile (3.0 g, 22.53 mmol) and tetrabutylammonium hydrogen sulfate (765 mg, 2.25 mmol) in toluene (60 mL). The reaction mixture was stirred at RT for 2 hours. The aqueous layer was removed and extracted twice with EtOAc. The organic layers were combined and washed with a saturated aqueous solution of NH4Cl and brine, and then dried (MgSO4) and concentrated to give the title compound as a colorless oil (4.37 g, 78%). HPLC (Method A) Rt 4.7 min (purity: 95.2%). 1H NMR (CDCl3, 300 MHz) δ 7.65 (d, J=8.4 Hz, 2H), 7.50 (d, J=8.4 Hz, 2H), 4.68 (s, 2H), 4.05 (s, 2H), 1.50 (s, 9H).

Workup

  1. customThe aqueous layer was removed
  2. extractionextracted twice with EtOAc
  3. washwashed with a saturated aqueous solution of NH4Cl and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a112c0de313f4a5f99e95350df237e64
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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