Hydrochloric Acid → 2-(1-Propenyl)-4-(4-fluorophenoxy)phenol

HRID 744705Notes

Reaction equation

HRID 744705 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:18])[CH:2]=[CH2:3].Cl>[OH-].[K+].C(O)C>[CH:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[OH:18])=[CH:2][CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 186724734-(4-Fluorophenoxy)-2-(prop-2-en-1-yl)phenol

Product 1

HCID 543792502-(1-Propenyl)-4-(4-fluorophenoxy)phenol

Reagents, catalysts & solvents 1

HCID 21946426Potassium hydroxide ethanolSolvent

Procedure

A solution of 2-allyl-4-(4-fluorophenoxy)phenol, from above, in saturated KOH/ethanol (65 mls) was refluxed for 18 hrs. It was then cooled to r.t. and acidified to pH2 by that addition of 10% HCl The aqueous solution was then extracted with ethylacetate (3×200 mls). The organics were combined, dried with MgSO4 and concentrated to afford 17.52 g of 2-(1-propenyl)-4-(4-fluorophenoxy)phenol as a brownish oil which was used as is.

Workup

  1. extractionwas then extracted with ethylacetate (3×200 mls)
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6881ac7e202341088c86c3f24d3019ba
Source dataset
uspto-grants-1996_09
Patent number
US05559144

Reaction notes

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