Sodium Hydroxide → HCID 18412066, compound

HRID 992451Notes

Reaction equation

HRID 992451 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:16][C:17]#[CH:18])[O:12]C(C)(C)[O:10][C:9]2=[O:15])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:12])([CH2:16][C:17]#[CH:18])[C:9]([OH:15])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 18412031HCID 18412031, compound

Product 1

HCID 18412066HCID 18412066, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 530 mg 5-(4-chloro-phenyl)-2,2-dimethyl-5-prop-2-ynyl-(1,3)dioxolan-4-one in 10 ml tetrahydrofurane and 5 ml methanol is treated with 2 ml of 1N NaOH and heated at 60° C. for 1 hour. Then the solution is cooled down, diluted with water and washed with ether. Then the aqueous solution is acidified with 1N HCl and extracted with ethyl acetate. The extracts are dried over sodium sulfate and evaporated to obtain the 2-(4-chlorophenyl)-2-hydroxy-pent-4-ynoic acid of a brownish thick oil which is used for the next step.

Workup

  1. temperatureThen the solution is cooled down
  2. washwashed with ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extracts are dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-1260454b6bfb4fd9a1b489c5c8050bdc
Source dataset
uspto-grants-2002_10
Patent number
US06469005B1

Reaction notes

Loading…