Chloroform → HCID 9834706, compound

HRID 1073521Notes

Reaction equation

HRID 1073521 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH2:17]1[O:20][C@H:18]1[CH3:19].C(Cl)(Cl)Cl>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:17][C@H:18]([OH:20])[CH2:19][O:14][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 132544-PhenoxyphenolHCID 14798Sodium HydroxideHCID 146262(2S)-2-Methyloxirane2×

Product 1

HCID 9834706HCID 9834706, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 4-phenoxyphenol (2.14 g, 11.5 mmol) in toluene (7 ml) was poured into an aqueous solution (3 ml) of sodium hydroxide (0.92 g, 23.0 mmol), and (S)-(-)propylene oxide (1.0 g, 17.24 mmol; a reagent manufactured by Aldrich; [α]D20 =-7.2° (CHCl3, c=1)) was added thereto while stirring. To the resultant mixture, tetra-n-butyl-ammonium bromide (185 mg) was added, and the mixture was stirred at room temperature for 12 hours, followed by addition of (S)-(-)-propylene oxide (1 g). After stirring at room temperature for 6 hours, the reaction mixture was vigorously stirred with addition of water (20 ml) and toluene (20 ml). The toluene layer was separated and washed with a 20 % aqueous sodium hydroxide solution and an aqueous sodium chloride solution in order and dried over magnesium sulfate. Removal of the solvent gave crude (S)-(+)-1-methyl-2-(4-phenoxyphenoxy)ethanol (2.35 g), which was further purified by silica gel column chromatography to give (S)-(+)-1-methyl-2-(4-phenoxyphenoxy)ethanol (1.97 g). [α]D23 =+14.0° (CHCl3, c=1). ee.: 72.9%.

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. stirringAfter stirring at room temperature for 6 hours
  3. customThe toluene layer was separated
  4. washwashed with a 20 % aqueous sodium hydroxide solution
  5. dry with materialan aqueous sodium chloride solution in order and dried over magnesium sulfate
  6. customRemoval of the solvent
  7. customgave crude (S)-(+)-1-methyl-2-(4-phenoxyphenoxy)ethanol (2.35 g), which
  8. customwas further purified by silica gel column chromatography

Sources & evidence

ORD record
ord-105b2cd6622c4caba86a3a7135fd0445
Source dataset
uspto-grants-1990_11
Patent number
US04970222

Reaction notes

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