Sodium Hydroxide → HCID 20569047, compound

HRID 1578128Notes

Reaction equation

HRID 1578128 reaction equation
[CH:1]#[C:2][CH:3]([OH:5])[CH3:4].[C:6]1([C:16](Cl)=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[OH-].[Na+]>>[C:6]1([C:16]([O:5][CH:3]([CH3:4])[C:2]#[CH:1])=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 162393-Butyn-2-olHCID 701461-Naphthalenecarbonyl chloride

Product 1

HCID 20569047HCID 20569047, compound

Conditions

Temperature
-10 °C

Procedure

A suspension of 5.3 g of 1-butyn-3-ol and 5 g of 1-naphthoyl chloride is cooled to -10° C. and 3.1 ml. of 35% sodium hydroxide are slowly added dropwise. The mixture is warmed to room temperature and stirred until it is neutral. The mixture is poured into ice-water and then extracted with ether. The ether solution is washed with 10% sodium hydroxide and with water and dried. After the ether is distilled off, the residue is recrystallized from methanol to yield 1-methyl-2-propynyl 1-naphthoate, m.p. 66°-68° C.

Workup

  1. temperatureThe mixture is warmed to room temperature
  2. extractionextracted with ether
  3. washThe ether solution is washed with 10% sodium hydroxide and with water
  4. customdried
  5. distillationAfter the ether is distilled off
  6. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-b873fcd09bc94426b194547bf28ab302
Source dataset
uspto-grants-1981_09
Patent number
US04291058

Reaction notes

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