Water → HCID 21960827, compound

HRID 2211574Notes

Reaction equation

HRID 2211574 reaction equation
[CH2:1]([O:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Br:22]Br.O>ClCCl>[Br:22][C:12]1[C:11]([CH3:14])=[CH:10][C:9]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[C:8]([O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 21960830HCID 21960830, compound

Product 1

HCID 21960827HCID 21960827, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Next, 91 g (0.31 mol) of the 1,2-di(n-hexyloxy)-4-methylbenzene was dissolved in 270 g of dichloromethane. While cooling in an ice/water bath, 49.7 g (0.31 mol) of bromine was added dropwise at a temperature below 10° C. After the completion of dropwise addition, 200 g of water was added. The organic layer was separated and washed with a saturated sodium hydrogen carbonate aqueous solution. The organic layer was concentrated on a rotary evaporator, yielding 120 g of an oily matter. This was distilled in vacuum (boiling point 180–190° C./0.5 Torr), obtaining 104 g (yield 90%) of 5-bromo-1,2-di(n-hexyloxy)-4-methylbenzene.

Workup

  1. temperatureWhile cooling in an ice/water bath
  2. additionwas added
  3. customThe organic layer was separated
  4. washwashed with a saturated sodium hydrogen carbonate aqueous solution
  5. concentrationThe organic layer was concentrated on a rotary evaporator
  6. customyielding 120 g of an oily matter
  7. distillationThis was distilled in vacuum (boiling point 180–190° C./0.5 Torr)

Sources & evidence

ORD record
ord-aa3accb67669411f94424e816cb2d0ed
Source dataset
uspto-grants-2006_09
Patent number
US07101651B2

Reaction notes

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