Hydrochloric Acid → HCID 21553948, compound

HRID 267794Notes

Reaction equation

HRID 267794 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](C([O-])=O)[C:5]([O:8][CH:9]([C:11]#[N:12])[CH3:10])=[CH:6][CH:7]=1.[OH-:16].[K+].Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([OH:16])[C:5]([O:8][CH:9]([C:11]#[N:12])[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21553930HCID 21553930, compound

Product 1

HCID 21553948HCID 21553948, compound

Procedure

3-Chloro-6-(1-cyanoethoxy)-phenyl-formate (56.4 g., 0.25 mole) is added to a solution of 85% potassium hydroxide (17.1 g., 0.26 mole) in 95% alcohol (200 ml.) at ambient temperature, and the mixture then stirred overnight under nitrogen. The reaction mixture is treated with a slight excess of dilute hydrochloric acid, and most of the alcohol removed under reduced pressure. The product is extracted with ether, the ethereal extract is washed with water, then with 5% sodium carbonate solution and again with water. The ethereal extract then is dried over magnesium sulfate and then over calcium sulfate and the ether removed by evaporation yielding 3-chloro-6-(1-cyanoethoxy)-phenol, which is crystallized from chloroform-petroleum ether.

Workup

  1. custommost of the alcohol removed under reduced pressure
  2. extractionThe product is extracted with ether
  3. extractionthe ethereal extract
  4. washis washed with water
  5. extractionThe ethereal extract
  6. dry with materialthen is dried over magnesium sulfate
  7. customover calcium sulfate and the ether removed by evaporation

Sources & evidence

ORD record
ord-1cb5e45a445c43dda746547f627744ac
Source dataset
uspto-grants-1976_03
Patent number
US03944560

Reaction notes

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