Benzoate → 4-(2,4-Nonadiynyloxy)benzoic acid

HRID 2640

Reaction equation

HRID 2640 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([OH:12])[CH3:11].[OH-].[K+].Cl>O>[CH2:10]([O:12][C:5]1[CH:6]=[CH:7][C:2]([C:1]([OH:9])=[O:8])=[CH:3][CH:4]=1)[C:11]#[C:1][C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 242BenzoateHCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium Hydroxide

Product 1

HCID 189358794-(2,4-Nonadiynyloxy)benzoic acidYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

In a flask were placed 4.0 g (0.014 mole) of the benzoate derivative obtained and 18 ml of ethanol and while stirring the mixture at room temperature, an aqueous solution composed of 2.0 g (0.36 mole) of potassium hydroxide and 20 ml of water was added to the mixture. After stirring the mixture for 24 hours at 40° C. Twenty (20) ml of water was added to the mixture followed by ice-cooled. When the reaction mixture was acidified with concentrated hydrochloric acid, white crystals formed. The crystals were recovered by filtration, washed with water, and dried. Thus, 3.2 g (yield 89.3%) of the desired product could be obtained. The melting point was 165°-166° C.

Workup

  1. customIn a flask were placed
  2. additionwas added to the mixture
  3. temperaturecooled
  4. customformed
  5. filtrationThe crystals were recovered by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-a31f86da055a41eca836286b819df96e
Source dataset
uspto-grants-1998_03
Patent number
US05730903

Linked notes

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