Potassium Hydroxide → HCID 13092093, compound

HRID 485159Notes

Reaction equation

HRID 485159 reaction equation
[CH:1]([C:3]1[C:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])=[O:2].[OH-].[K+]>C(O)C>[CH:1]([C:3]1[C:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20271552Ethyl 5-(2-formyl-3-benzyloxyphenoxy)pentanoate

Product 1

HCID 13092093HCID 13092093, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 5-(2-formyl-3-benzyloxyphenoxy)pentanoate (3.61 g, 0.01 M), potassium hydroxide (1.19 g, 0.021 M) and ethanol (40 ml) were stirred at 50°-60° C. for 5 hours. The ethanol was then removed in vacuo, the residue dissolved in water (50 ml) and the solution extracted with ether (2×80 ml). The aqueous layer was then acidified by the addition of 2N aqueous hydrochloric acid and the product extracted with ether (3×50 ml), and the combined extracts washed with water to neutrality, dried, and concentrated in vacuo to give 5-(2-formyl-3-benzyloxyphenoxy) pentanoic acid, 3.0 g, 91% as a yellow oil which crystallised on standing. The crude solid was crystallised from benzene/petroleum spirit 30°-40° C. to give pale cream crystals m.p. 110° C.

Workup

  1. customThe ethanol was then removed in vacuo
  2. dissolutionthe residue dissolved in water (50 ml)
  3. extractionthe solution extracted with ether (2×80 ml)
  4. additionThe aqueous layer was then acidified by the addition of 2N aqueous hydrochloric acid
  5. extractionthe product extracted with ether (3×50 ml)
  6. washthe combined extracts washed with water to neutrality
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94ad8a2b6f42465f8fc2b98b567d16ee
Source dataset
uspto-grants-1985_08
Patent number
US04535183

Reaction notes

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