Hydrochloric Acid → 5-Methoxy-3,3-dimethyl-5-oxopentanoic acid

HRID 507098Notes

Reaction equation

HRID 507098 reaction equation
[CH3:1][C:2]1([CH3:10])[CH2:8][C:7](=[O:9])[O:6][C:4](=[O:5])[CH2:3]1.[CH3:11][O-:12].[Na+].C(OCC)C.Cl>CO>[CH3:11][O:12][C:7](=[O:9])[CH2:8][C:2]([CH3:10])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 778133,3-Dimethylglutaric anhydrideHCID 10942334Sodium Methoxide

Product 1

HCID 5478975-Methoxy-3,3-dimethyl-5-oxopentanoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 3,3-dimethylglutaric anhydride (1.00 g, 7.03 mmol) and sodium methoxide (2.5 mL, 14.1 mmol, 30 wt % in methanol) in methanol (20 mL) and heat at reflux for 3 h. Cool the reaction to room temperature and pour into ice water (100 mL). Add diethyl ether (25 mL) and adjust the pH of the mixture to pH=2 with 2 N HCl (10 mL) and separate the layers. Extract the aqueous layer with diethyl ether (25 mL) and combine the organic layers, dry over sodium sulfate, filter and remove the solvent under reduced pressure to afford 3,3-dimethylpentanedioic acid monomethyl ester as a colorless oil (0.827 g, 68%): 1H NMR (CDCl3, 300 MHz) δ 1.14 (s, 6H), 2.46 (s, 2H), 2.48 (s, 2H), 3.67 (s, 3H), 10.9 (br s, 1H); APCI MS (Negative mode) m/z 173 [C8H14O4−H]−.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureCool
  3. customthe reaction to room temperature
  4. customseparate the layers
  5. extractionExtract the aqueous layer with diethyl ether (25 mL)
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-1e44b4ef6d004007be4a10cf508c03ea
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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