Water → (1-{[(3-Phenoxyphenyl)methoxy]methyl}cyclopropyl)methanol

HRID 1200061Notes

Reaction equation

HRID 1200061 reaction equation
[OH:1][CH2:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[H-].[Na+].[O:10]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:1][CH2:2][C:3]1([CH2:6][O:7][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[C:17]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:18]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 41014371,1-Bis(hydroxymethyl)cyclopropane

Product 1

HCID 13849406(1-{[(3-Phenoxyphenyl)methoxy]methyl}cyclopropyl)methanolYield 40.5%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1,1-dihydroxymethylcyclopropane (3 g) in tetrahydrofuran (20 cm3) was added dropwise to a suspension of sodium hydride (0.35 g) in tetrahydrofuran (30 cm3). After effervescence has ceased, tetrabutylammonium iodide (1 g) was added to the grey suspension followed by a solution of 3-phenoxybenzyl bromide (3.88 g) in tetrahydrofuran (15 cm3) at the ambient temperature and the mixture stirred for a further 2 hours. The mixture was poured into water and extracted with ethylacetate. The extracts were combined, dried over magnesium sulphate and concentrated by evaporation of the solvent, and the residual oil purified by column chromatography using a silica gel column eluting first with dichloromethane, followed then by ethylacetate, to give 1-hydroxymethyl-1-(3-phenoxybenzyloxymethyl)cyclopropane (1.7 g).

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated by evaporation of the solvent
  4. customthe residual oil purified by column chromatography
  5. washeluting first with dichloromethane

Sources & evidence

ORD record
ord-e913a4ac14e54dcd8e5b85f62f950959
Source dataset
uspto-grants-1990_02
Patent number
US04904677

Reaction notes

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