Water → 2-(2-Bromo-3-methylphenyl)ethan-1-ol

HRID 427517Notes

Reaction equation

HRID 427517 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10](OCC)=[O:11].O.[OH-].[Na+]>O1CCCC1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][OH:11]

Participants

5

Reactant 3

HCID 962Water2×HCID 14798Sodium HydroxideHCID 18357438Ethyl 2-(2-bromo-3-methylphenyl)acetate

Product 1

HCID 226725712-(2-Bromo-3-methylphenyl)ethan-1-olYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

LiAIH4 (3.1 g, 0.083 mol) was suspended in dry tetrahydrofuran (100 ml) in argon atmosphere. Ethyl 2-(2-bromo-3-methylphenyl)acetate (8.5 g, 0.033 mol) solved in dry tetrahydrofuran (50 ml) was added and the mixture was stirred at room temperature for 4 h. The mixture was cooled on ice and 3.1 ml of water was added dropwise, followed by 3.1 ml of 15% sodium hydroxide and then 9.3 ml of water. After 15 h. the solids were removed by filtration and washed thoroughly with tetrahydrofuran. The filtrate was removed under reduced pressure. Purification of the residue by filtrating through silica gel using methylene chloride:methanol (9:1) as eluent gave 7.0 g (98.6%) of the title compound as an oil.

Workup

  1. additionwas added
  2. additionwas added dropwise
  3. customAfter 15 h. the solids were removed by filtration
  4. washwashed thoroughly with tetrahydrofuran
  5. customThe filtrate was removed under reduced pressure
  6. customPurification of the residue
  7. filtrationby filtrating through silica gel

Sources & evidence

ORD record
ord-80bdd8ef9aec44e38f51ec468b0688a9
Source dataset
uspto-grants-2001_11
Patent number
US06313137B1

Reaction notes

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