Potassium Hydroxide → 4-(2,4-Dibenzyloxyphenyl)-2,4-dioxobutanoic acid

HRID 322857Notes

Reaction equation

HRID 322857 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]=1[C:23](=[O:32])[CH2:24][C:25](=[O:31])[C:26]([O:28]CC)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CO>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:12]=[CH:11][C:10]=1[C:23](=[O:32])[CH2:24][C:25](=[O:31])[C:26]([OH:28])=[O:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11796971Ethyl 4-(2,4-dibenzyloxyphenyl)-2,4-dioxobutanoate

Product 1

HCID 220103044-(2,4-Dibenzyloxyphenyl)-2,4-dioxobutanoic acidYield 32.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 4-(2,4-dibenzyloxyphenyl)-2,4-dioxobutanoate (2 g) in methanol (100 mL) is treated with 10% aqueous potassium hydroxide (10 mL) and the mixture stirred at room temperature for 18 hours. The reaction mixture is evaporated to low bulk and the residue partitioned between ethyl acetate (100 mL) and 1 N hydrochloric acid (50 mL). The organic phase is washed with water, dried over magnesium sulphate and evaporated in vacuo. The residue iscrystallised from a mixture of ethyl acetate and cyclohexane to give 4-(2,4-dibenzyloxyphenyl)-2,4-dioxobutanoic acid (0.6 g), in the form of a white solid, m.p. 160-164° C. [Elemental analysis:- C,71.3; H,4.93%. Calculated:- C,71.3; H,4.99%].

Workup

  1. customThe reaction mixture is evaporated to low bulk
  2. customthe residue partitioned between ethyl acetate (100 mL) and 1 N hydrochloric acid (50 mL)
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated in vacuo
  6. additionThe residue iscrystallised from a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-306fdc4d38f246418b60d7b78b8abe5b
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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