4-Hydroxybenzoic Acid → 4-(Cyanopropyloxy)benzoic acid

HRID 1634100Notes

Reaction equation

HRID 1634100 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CC[O-].[Na+].Br[CH2:16][CH2:17][CH2:18][C:19]#[N:20]>CCO>[C:19]([CH2:18][CH2:17][CH2:16][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)#[N:20]

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 214124-BromobutyronitrileHCID 2723922Sodium ethoxide

Product 1

HCID 146503364-(Cyanopropyloxy)benzoic acidYield 58.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 4-hydroxybenzoic acid (40 mmol) in absolute EtOH (350 mL) was added solid NaOEt (84 mmol). After 15 minutes, 4-bromobutyronitrile (40 mmol) was added and the mixture was heated overnight at 90° C. on an oil bath. The mixture was cooled to room temperature, volatiles were removed, the residue was taken up in ice and adjusted to pH 6 with 1N sulfuric acid. Solids were collected by vacuum filtration, washed with water and dried to give 4-(cyanopropyloxy)benzoic acid (4.8 g, 58%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customvolatiles were removed
  3. filtrationSolids were collected by vacuum filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-6b5ec3adc68d47aaa283307c9f615fdb
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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