Salicyl Alcohol → 5-Bromo-2-hydroxybenzyl alcohol

HRID 1856057Notes

Reaction equation

HRID 1856057 reaction equation
[Br:1]Br.C(Cl)(Cl)(Cl)Cl.[OH:8][CH2:9][C:10]1[C:15]([OH:16])=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Ca+2]>C(Cl)Cl>[Br:1][C:12]1[CH:13]=[CH:14][C:15]([OH:16])=[C:10]([CH:11]=1)[CH2:9][OH:8]

Participants

6

Reactant 4

HCID 5146Salicyl AlcoholHCID 5943Carbon Tetrachloride2×HCID 10112Calcium CarbonateHCID 24408Bromine

Product 1

HCID 753425-Bromo-2-hydroxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

At 0°-5° C., 11.5 ml. of bromine in 100 ml. of carbon tetrachloride was added dropwise to a suspension of 24.8 g. of saligenin and 24 g. of calcium carbonate in a solvent mixture of 200 ml. of carbon tetrachloride and 220 ml. of methylene chloride. The reaction mixture was stirred for 24 hours at room temperature, then filtered, and the precipitate was washed with carbon tetrachloride. The CCl4 /CH2Cl2 phase was discarded. The solid substance was taken up in ethyl acetate/water, and the organic phase was separated, dried over magnesium sulfate, and evaporated to dryness. The residue was recrystallized from methylene chloride, thus obtaining colorless crystal flakes (24 g.). Melting point: 107°-109° C. (methylene chloride).

Workup

  1. customAt 0°-5° C.
  2. filtrationfiltered
  3. washthe precipitate was washed with carbon tetrachloride
  4. customthe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was recrystallized from methylene chloride
  8. customthus obtaining colorless crystal flakes (24 g.)

Sources & evidence

ORD record
ord-27c91e5160084866b02e05c434566626
Source dataset
uspto-grants-1980_08
Patent number
US04217360

Reaction notes

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