4-Bromophenol → HCID 54531626, compound

HRID 1769566Notes

Reaction equation

HRID 1769566 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.S(C1C=CC(C)=CC=1)(O[C@@H:13]([CH3:19])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C1(=O)CCCCC1>[CH3:19][C@@H:13]([O:7][C:6]1[CH:5]=[CH:4][C:3]([Br:8])=[CH:2][CH:1]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 54517469HCID 54517469, compound

Product 1

HCID 54531626HCID 54531626, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 7967CyclohexanoneSolvent

Procedure

A reaction vessel was charged with 10 g of p-bromophenol, 19 g of (S)-1-methylhexyl tosylate, 10 g of potassium carbonate and 150 ml of cyclohexanone, and the mixture was stirred under reflux for 15 hours (the starting materials were confirmed to have disappeared by GLC). The reaction liquid was filtered and the filter cake was washed with benzen. The washings and the filtrate were combined, washed with water and then dried over Glauber's salt. The solvents were distilled off and the residue was purified by way of column chromatography on silica gel (eluent:hexane) to obtain 14 g (89.4%) of (R)-4-(1-methylhexyl)oxybromobenzene.

Workup

  1. temperatureunder reflux for 15 hours (the starting materials
  2. customThe reaction liquid
  3. filtrationwas filtered
  4. washthe filter cake was washed with benzen
  5. washwashed with water
  6. dry with materialdried over Glauber's salt
  7. distillationThe solvents were distilled off
  8. customthe residue was purified by way of column chromatography on silica gel (eluent:hexane)

Sources & evidence

ORD record
ord-284c6a0a958542768476a083f3e85fc1
Source dataset
uspto-grants-1995_01
Patent number
US05382380

Reaction notes

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