Water → (4-Bromo-3-methylphenyl)methanol

HRID 538948Notes

Reaction equation

HRID 538948 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[C:16]([CH3:17])=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=1.O>C1COCC1>[Br:7][C:8]1[C:16]([CH3:17])=[CH:15][C:11]([CH2:12][OH:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 821314-Bromo-3-methylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 10987288(4-Bromo-3-methylphenyl)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (1.75 g, 46 mmol) was added in portions to a stirred solution of 4-bromo-5-methylbenzoic acid (10 g, 46 mmol) in THF (100 mL) at 0° C. After 15 min, H2O (50 mL) was added drop wise to the reaction which was then extracted with EtAOc (100 mL×3). The combined organic layers were washed with brine (200 mL×2), dried (Na2SO4), and concentrated under reduced pressure to yield compound 2 as a light yellow syrup (9.25 g, 46 mmol, 100% yield). 1H NMR, (400 MHz, CDCl3): δ 7.52 (d, J=8.2 Hz, 1H), 7.25 (d, J=2.4 Hz, 1H), 6.88-7.10 (m, 1H), 4.63 (s, 2H), 2.43 (s, 3H).

Workup

  1. customwise to the reaction which
  2. extractionwas then extracted with EtAOc (100 mL×3)
  3. washThe combined organic layers were washed with brine (200 mL×2)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84006c831baf4b84b5cbf7cfc22ea343
Source dataset
uspto-grants-2014_10
Patent number
US08865914B2

Reaction notes

Loading…