Calcium Carbonate → (3-Bromo-5-methylphenyl)methanol

HRID 564462Notes

Reaction equation

HRID 564462 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9]Br)[CH:3]=1.[O:11]1CCOCC1.C(=O)([O-])[O-].[Ca+2]>O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 10112Calcium CarbonateHCID 312751,4-DioxaneHCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzene

Product 1

HCID 22983157(3-Bromo-5-methylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-bromo-3-(bromomethyl)-5-methylbenzene (40.0 g, 151 mmol), 1,4-dioxane (150 mL), water (150 mL) and calcium carbonate (37.9 g, 379 mmol) was heated for 16 h at reflux. The mixture was filtered and the filtrate was concentrated in vacuum, then diluted with CH2Cl2 (150 mL). The organic layer was washed with HCl (2N, 50 mL) and a solution of saturated sodium bicarbonate (50 mL), dried (Na2SO4) and concentrated in vacuum to give 25.0 g of crude product (3-bromo-5-methylphenyl)methanol.

Workup

  1. temperaturewas heated for 16 h
  2. temperatureat reflux
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuum
  5. additiondiluted with CH2Cl2 (150 mL)
  6. washThe organic layer was washed with HCl (2N, 50 mL)
  7. dry with materiala solution of saturated sodium bicarbonate (50 mL), dried (Na2SO4)
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-739ce7e3838d4717abd5a6f7411d03f2
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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