Dimethyl Carbonate → 4-Tert-butyl-2-(carboxymethyl)benzoic acid

HRID 2236441Notes

Reaction equation

HRID 2236441 reaction equation
[Li].[C:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH3:15])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[C:16](=O)([O:19]C)[O:17]C>O1CCCC1>[C:2]([C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]([CH2:15][C:16]([OH:19])=[O:17])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 3028194LithiumHCID 119589774-Tert-butyl-2-methylbenzoic acid

Product 1

HCID 426258304-Tert-butyl-2-(carboxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

An amount of 26 mL (198 mmol) of Lithium diiopropylamide (Aldrich) is added to a three neck flask cooled to −40° C. To this is added drops wise, a mixture of 4-tert-butyl-2-methyl-benzoic acid 1.9 g (9.9 mmol) and dimethyl carbonate 3.3 mL (39.6 mmol) in 5 mL of tetrahydrofuran, while keeping the temperature at −60° C. After the addition, the temperature is kept between −40° C. to −60° C. for four hours, then brought to 0° C. and quenched with 25 mL of water. The mixture is allowed to stir at room temperature for two hours and acidify to pH 2 with hydrogen chloride, extracted 3× with ethyl acetate, dried over magnesium sulfate and evaporated.

Workup

  1. additionTo this is added drops wise
  2. customat −60° C
  3. additionAfter the addition
  4. custombrought to 0° C.
  5. customquenched with 25 mL of water
  6. extractionextracted 3× with ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-359040f52f1b4d788e15f8b89a4e9c58
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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