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Monobenzone → 1-Benzyloxy-4-(2-phenethyloxyethoxy)benzene

HRID 1905974
Notes
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Reaction equation

HRID 1905974 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:23][CH2:24][O:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=O)=O>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:23][CH2:24][O:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 132089412-Phenethyloxy-ethanol mesylate

Product 1

HCID 202137271-Benzyloxy-4-(2-phenethyloxyethoxy)benzeneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

10 g of 4-benzyloxyphenol in 120 ml of dimethylformamide were treated with 2.4 g of a 50% sodium hydride dispersion in mineral oil and the mixture was stirred for 5 minutes. 12.2 g of 2-(2-phenylethoxy)ethyl methanesulfonate [prepared as described in Example 1(a)] were added and the mixture was heated at 60° C. for 0.5 hour with stirring. The mixture was evaporated to dryness and the residue was partitioned between 2N sodium hydroxide and ethyl acetate. The organic phase was separated, washed well with water, dried over sodium sulfate, filtered and evaporated. The residue was recrystallized from methylcyclohexane to give 16.1 g (93%) of 1-benzyloxy-4-(2-phenethyloxyethoxy)benzene of melting point 46°-49° C.

Workup

  1. stirringwith stirring
  2. customThe mixture was evaporated to dryness
  3. customthe residue was partitioned between 2N sodium hydroxide and ethyl acetate
  4. customThe organic phase was separated
  5. washwashed well with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was recrystallized from methylcyclohexane

Sources & evidence

ORD record
ord-dbb226c043e54d2d8a5acf57d9efecc7
Source dataset
uspto-grants-1987_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04649160

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes