4-Bromophenol → 1-Bromo-4-[(2-ethylhexyl)oxy]benzene

HRID 232900Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:12][CH:13]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15]>COCCO>[CH2:14]([CH:13]([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

A 1 l sulfonating flask equipped with stirrer, condenser, dropping funnel and internal thermometer is charged with 86.5 g (0.5 mol) of 4-bromophenol in 500 ml of methylcellosolve. After the mixture is heated to 60° C., 70.0 g of 30% NaOH (0.53 mol) are slowly run in. Stirring is continued for 15 minutes before 116.8 g (0.575 mol) of 3-bromomethylheptane are added dropwise over a period of 45 minutes. The reaction is continued overnight at 100° C. The thin-layer chromatogram shows almost quantitative conversion. Solvent and excess bromide are removed in vacuo, and the residue (oil) is taken up in 600 ml of toluene. The resulting solution is extracted three times with water. The organic phase is dried over sodium sulfate and evaporated to dryness to give 119.3 g (84% of theory) of 4-(2-ethylhexyloxy)bromobenzene as a light yellow oil.

Workup

customequipped with stirrer, condenser
additionare added dropwise over a period of 45 minutes
customSolvent and excess bromide are removed in vacuo
extractionThe resulting solution is extracted three times with water
dry with materialThe organic phase is dried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-002a73c05dcb4467af5ba441018d7825
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05591850

Reaction notes

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