Potassium Hydroxide → 4-[4-(4-Trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoic acid

HRID 638509Notes

Reaction equation

HRID 638509 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:24]=[CH:23][C:11]([O:12][CH:13]([CH3:22])[CH:14]([OH:21])[CH2:15][C:16]([O:18]CC)=[O:17])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[OH-].[K+].OC(CC)CC(O)=O>CO>[F:1][C:2]([F:27])([F:28])[C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:24]=[CH:23][C:11]([O:12][CH:13]([CH3:22])[CH:14]([OH:21])[CH2:15][C:16]([OH:18])=[O:17])=[CH:10][CH:9]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 1078023-Hydroxyvaleric acidHCID 12856783Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate

Product 1

HCID 128567844-[4-(4-Trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7.0 g of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-3-hydroxypentanoate and 1.74 g of 85% KOH in 30 ml ag. methanol was stirred at room temperature for 1.5 hrs. The mixture was concentrated, poured into water and acidified. The product was dissolved in ether, washed with brine, dried over MgSO4 and vacuum evaporated to yield 6.0 of product which was identified as the subject 3-hydroxypentanoic acid.

Workup

  1. concentrationThe mixture was concentrated
  2. additionpoured into water
  3. dissolutionThe product was dissolved in ether
  4. washwashed with brine
  5. dry with materialdried over MgSO4 and vacuum
  6. customevaporated
  7. customto yield 6.0 of product which

Sources & evidence

ORD record
ord-471c0fe6e02444de82f2b5a29d2ee678
Source dataset
uspto-grants-1985_12
Patent number
US04561882

Reaction notes

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