2-Bromoethanol → HCID 89464203, compound

HRID 881981Notes

Reaction equation

HRID 881981 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].BrC[CH2:16][OH:17].[C:18]([O-])([O-])=O.[K+].[K+]>CC#N>[OH:17][CH2:16][CH2:13][O:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([O:1][CH3:18])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

Product 1

HCID 89464203HCID 89464203, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-hydroxy-5-methoxybenzoate (1.82 g, 10 mmol) and 2-bromoethanol (2.5 g, 20 mmol) in CH3CN (20 ml) was added K2CO3 (4.2 g, 0.03 mol) and the reaction mixture was heated to 80° C. overnight. After to cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was purified using normal phase chromatography eluting with petroleum ether and increasing amounts of ethyl acetate to give compound methyl 3-(2-hydroxyethoxy)-5-methoxybenzoate (1.0 g).

Workup

  1. temperatureAfter to cooling to room temperature
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified
  5. washeluting with petroleum ether
  6. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-48ddd5f1a1884a278f90d093c9838034
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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