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Potassium Iodide → ethyl (RS)-4-(3-benzyloxyphenoxy)-4-phenylbutanoate

HRID 322876
Notes
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Reaction equation

HRID 322876 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(C(C)=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 138048Benzyl 3-hydroxyphenyl etherHCID 12847348Ethyl 4-chloro-4-phenylbutanoate

Product 1

HCID 23204045ethyl (RS)-4-(3-benzyloxyphenoxy)-4-phenylbutanoateYield 17.1%

Reagents, catalysts & solvents 1

HCID 6569
Methyl Ethyl Ketone
Solvent

Procedure

A mixture of 3-benzyloxyphenol (3 g), ethyl (RS)-4-chloro-4-phenylbutanoate (4.53 g), potassium carbonate (4.14 g), potassium iodide (100 mg) and methyl ethyl ketone (100 mL) is heated at reflux for 40 hours. The mixture is evaporated to dryness and the residue is partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer is dried over magnesium sulphate, filtered, and concentrated in vacuo. Flash chromatography of the resulting oil, eluting with a mixture of ethyl acetate and cyclohexane (1:19 v/v), gives ethyl (RS)-4-(3-benzyloxyphenoxy)-4-phenylbutanoate (1 g), in the form of a yellow oil.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 40 hours
  3. customThe mixture is evaporated to dryness
  4. customthe residue is partitioned between ethyl acetate (200 mL) and water (200 mL)
  5. dry with materialThe organic layer is dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washFlash chromatography of the resulting oil, eluting with a mixture of ethyl acetate and cyclohexane (1:19 v/v)

Sources & evidence

ORD record
ord-3ba37cce7b7d4a3497a10cae57bd6450
Source dataset
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06211234B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes