Water → 4-[2-(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)ethyl]phenol

HRID 2227103Notes

Reaction equation

HRID 2227103 reaction equation
[CH3:1][C:2]([CH3:22])=[CH:3][CH2:4][CH2:5][C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)[CH2:8][CH:7]=1.B(Br)(Br)Br.O>ClCCl>[CH3:1][C:2]([CH3:22])=[CH:3][CH2:4][CH2:5][C:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=2)[CH2:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 184718172-(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)ethyl-4-methoxybenzene

Product 1

HCID 184718234-[2-(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)ethyl]phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of anisole 2F (R=4-Methyl-3-pentenyl) (6 g) in dichloromethane (100 mL) and cooled in an ice bath is added a 1M solution of boron tribromide (3.4 mL). The solution is stirred for one hour, then poured into water. The reaction mixture is extracted with dichloromethane and dried over magnesium sulfate. The solution is concentrated in vacuo. The product is recrystallized from hexane.

Workup

  1. extractionThe reaction mixture is extracted with dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe solution is concentrated in vacuo
  4. customThe product is recrystallized from hexane

Sources & evidence

ORD record
ord-cd9462bf4bf542ca9fff7f6eea480cb0
Source dataset
uspto-grants-2002_07
Patent number
US06413448B1

Reaction notes

Loading…