Potassium Carbonate → HCID 11817603, compound

HRID 1250096Notes

Reaction equation

HRID 1250096 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[OH:10][CH2:11][C:12]1[C:13]([CH3:19])=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:6]([O:5][C:3](=[O:4])[CH2:2][O:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][OH:10])[C:13]=1[CH3:19])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 130594263-(Hydroxymethyl)-2-methylphenol

Product 1

HCID 11817603HCID 11817603, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Tert-butyl bromoacetate (75 g, 385 mmol) was added to a solution/suspension of 3-hydroxymethyl-2-methylphenol (46.6 g, 337 mmol) and finely powdered potassium carbonate (60 g) in acetone (500 mL). The mixture was heated at reflux for about 40 hours or until the reaction was complete. The solids were filtered, and the liquid residue was evaporated. Purification of the residue by silica gel chromatography, eluting with acetone/hexane, gave (3-hydroxymethyl-2-methylphenoxy)acetic acid tert-butyl ester as a pale yellow oil (80.1 g, 96%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for about 40 hours or until the reaction
  3. filtrationThe solids were filtered
  4. customthe liquid residue was evaporated
  5. customPurification of the residue by silica gel chromatography
  6. washeluting with acetone/hexane

Sources & evidence

ORD record
ord-5079a31faf5740f697d74fd71153972a
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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