Hydrochloric Acid → Methyl 3-bromo-6-(2-hydroxyethoxy)-2-methylbenzoate

HRID 577569Notes

Reaction equation

HRID 577569 reaction equation
[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([C:9]([O:12][CH2:13][CH2:14][O:15]C2CCCCO2)=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl>CO>[Br:1][C:2]1[C:3]([CH3:22])=[C:4]([C:9]([O:12][CH2:13][CH2:14][OH:15])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86723693methyl 3-bromo-2-methyl-6-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]benzoate

Product 1

HCID 86723795Methyl 3-bromo-6-(2-hydroxyethoxy)-2-methylbenzoateYield 110%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 3-bromo-2-methyl-6-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]-benzoate (Cpd HH, 162 mg, 0.434 mmol) in MeOH (4 mL) was treated with 6N HCl (0.2 mL) and stirred at room temperature for 30 minutes. The solvent was concentrated in vacuum to 1 mL and the solution partitioned between DCM (25 mL) and NaHCO3 (sat., aq., 25 mL). The organic layer was concentrated under vacuum to give methyl 3-bromo-6-(2-hydroxyethoxy)-2-methylbenzoate (126a, 138 mg, 110% yield) as a colorless oil.

Workup

  1. concentrationThe solvent was concentrated in vacuum to 1 mL
  2. customthe solution partitioned between DCM (25 mL) and NaHCO3 (sat., aq., 25 mL)
  3. concentrationThe organic layer was concentrated under vacuum

Sources & evidence

ORD record
ord-82e81d7a35d043ebabf23995d0eabdc3
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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