Hydrochloric Acid → 1-(3-Bromo-4-methylphenyl)ethan-1-ol

HRID 1242820Notes

Reaction equation

HRID 1242820 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:16])=[O:15])=[CH:10][C:9]=1[Br:17].Cl>CCOCC>[Br:17][C:9]1[CH:10]=[C:11]([CH:14]([OH:15])[CH3:16])[CH:12]=[CH:13][C:8]=1[CH3:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 33094011-(3-Bromo-4-methylphenyl)ethan-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 219403321-(3-Bromo-4-methylphenyl)ethan-1-olYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminum hydride (6.45 g, 170 mmol) was added to a 250 mL round-bottom flask equipped with a magnetic stirrer bar and a septum. The flask was dried under vacuum and then filled with nitrogen. Anhydrous ether (50 mL) was first injected into the flask. Subsequently, a solution of 3-bromo-4-methylacetophenone (38 g, 180 mmol) in anhydrous ether (50 mL) was injected into the flask dropwise. The reaction mixture was stirred until no more gas was generated. The mixture was poured into a dilute HCl aqueous solution (240 mL), extracted with ethyl acetate (4×30 mL), washed over a saturated NH4Cl aqueous solution (50 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum to give a crude product. The crude product was further purified by distillation under reduced pressure (130° C., 4 mm Hg) to give 31.35 g (81% yield) of the desired product. 1H NMR (300 MHz, CDCl3) δ 1.47 (3H, t, J=6.4 Hz), 1.76 (1H, s), 2.38 (3H, s), 4.84 (1H, q, J=6.4 Hz), 7.20 (2H, s), 7.55 (1H, s); 3C NMR (75 MHz, CDCl3) δ 22.54, 25.16, 69.33, 124.30, 124.93, 129.34, 130.82, 136.88, 145.27; IR (neat) 3024 (s), 2997 (s), 2927 (m), 1605 (w), 1562 (w), 1494 (m), 1452 (m), 1381 (m), 1331 (w), 1255 (m), 1091 (m), 1038 (m), 1009 (m), 908 (m), 822 (m), 733 (s) cm−1; MS m/z 214 (M+), 199, 197, 171, 169, 119, 91; HRMS calcd for C9H11OBr 213.9993, found 213.9995.

Workup

  1. customequipped with a magnetic stirrer bar
  2. customThe flask was dried under vacuum
  3. additionfilled with nitrogen
  4. extractionextracted with ethyl acetate (4×30 mL)
  5. washwashed over a saturated NH4Cl aqueous solution (50 mL)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customto give a crude product
  9. distillationThe crude product was further purified by distillation under reduced pressure (130° C., 4 mm Hg)

Sources & evidence

ORD record
ord-5cde4ecc87554dc986b8622818c162cf
Source dataset
uspto-grants-2006_10
Patent number
US07115762B2

Reaction notes

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