Water → 2-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenol

HRID 81807Notes

Reaction equation

HRID 81807 reaction equation
[CH3:1][Mg]Br.[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:6]=1[C:13](=[O:15])[CH3:14].[Cl-].[NH4+].O>C(OCC)C.O1CCCC1>[OH:15][C:13]([C:6]1[C:7]([O:11][CH3:12])=[CH:8][CH:9]=[CH:10][C:5]=1[OH:4])([CH3:1])[CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 697091-(2-Hydroxy-6-methoxyphenyl)ethan-1-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 595986452-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl magnesium bromide (24 mL of a 3M solution in diethyl ether, 72.2 mmol) in anhydrous tetrahydrofuran (20 mL) at 0° C. was added a solution of 2′-hydroxy-6′-methoxyacetophenone (4 g, 24.1 mmol) in anhydrous tetrahydrofuran (40 mL), maintaining the temperature below 11° C. during the addition. After stirring for 1.5 hours at room temperature, a solution of 10% ammonium chloride (30 mL) was added slowly maintaining the temperature below 22° C. with the use of an ice bath. Water (300 mL) was slowly added and the reaction was extracted twice with ethyl acetate. The combined ethyl acetate layers were washed with water, brine, dried using anhydrous sodium sulfate and concentrated to give 2-(1-Hydroxy-1-methyl-ethyl)-3-methoxy-phenol (4.52 g) as pale yellow solid.

Workup

  1. temperaturemaintaining the temperature below 11° C.
  2. additionduring the addition
  3. temperaturemaintaining the temperature below 22° C. with the use of an ice bath
  4. extractionthe reaction was extracted twice with ethyl acetate
  5. washThe combined ethyl acetate layers were washed with water, brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29f109a19c9c428999781c80409eae9c
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

Loading…