Water → HCID 68223692, compound

HRID 1501132Notes

Reaction equation

HRID 1501132 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[CH:3]=1.[CH3:11][Mg]Br.O>O1CCCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH3:11])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 135551504-Bromo-2-methylbenzaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 68223692HCID 68223692, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-bromo-2-methylbenzaldehyde (1 g, 5 mmol) in tetrahydrofuran (30 mL) was added methylmagnesium bromide (3N in tetrahydrofuran, 2 mL) at −40° C. Then the mixture was stirred at 25° C. for 3 hours. Water (15 mL) was added to the mixture and then extracted with ethyl acetate (35 mL×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuo and purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give 1-(4-bromo-2-methylphenyl)ethanol (600 mg, 56%).

Workup

  1. extractionextracted with ethyl acetate (35 mL×3)
  2. dry with materialThe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-6d706e9608b8471f85cbfea18ba45a95
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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