Hydrochloric Acid → (4-Bromo-3-methylphenyl)methanol

HRID 439785Notes

Reaction equation

HRID 439785 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6](OCC)=[O:7])=[CH:4][C:3]=1[CH3:13].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>CCOCC.O>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH3:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 21729626Ethyl 4-bromo-3-methylbenzoate

Product 1

HCID 10987288(4-Bromo-3-methylphenyl)methanolYield 91.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethyl 4-bromo-3-methylbenzoate (14 g, 0.058 mol) was dissolved in ether (200 ml). Under ice-cooling, to the obtained solution was added lithium aluminium hydride (1.8 g, 0.046 mol) little by little, and under this state, the mixture was stirred for 1 hour. After decomposing excessive lithium aluminium hydride with ethyl acetate, water and 10% hydrochloric acid were added, and the mixture was extracted with ethyl acetate. After washing with water and saturated aqueous sodium chloride solution, the extract was dried over anhydrous sodium sulfate, and the solvent was distilled away. The residue was separated and purified by using a column chromatography (ethyl acetate:n-hexane=1:3) to give the title compound (10.6 g, 0.053 mol).

Workup

  1. temperatureUnder ice-cooling, to the obtained solution
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washAfter washing with water and saturated aqueous sodium chloride solution
  5. dry with materialthe extract was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away
  7. customThe residue was separated
  8. custompurified

Sources & evidence

ORD record
ord-512b6843f0d7443c99f651cbb998b3aa
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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