Hydrochloric Acid → 3-(Benzyloxy)-2,2-dimethylpropanoic acid

HRID 386605Notes

Reaction equation

HRID 386605 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13]C)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1>[CH2:1]([O:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 59267989Methyl 3-(benzyloxy)-2,2-dimethylpropanoate

Product 1

HCID 134782883-(Benzyloxy)-2,2-dimethylpropanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred solution of methyl 3-(benzyloxy)-2,2-dimethylpropanoate prepared according to Step A (952 mg, 4.28 mmol), in THF (11 mL) was added aqueous 1M NaOH (5.14 mL, 5.14 mmol). Little to no progress was seen at ambient temperature. Additional NaOH (˜7 mL, ˜7 mmol) was then added and the temperature was raised to 65° C., for 20 hours. After cooling to ambient temperature, the bulk of the THF was removed in vacuo. Aqueous 3M HCl (˜5 mL, ˜15 mmol) was then slowly added, resulting in the formation of a precipitate. This mixture was filtered through filter paper, and washed with a minimal amount of water. After placing under a strong vacuum for a few hours, the title compound was obtained. MS: m/z=231 (M+23 (Na+)).

Workup

  1. customwas seen at ambient temperature
  2. temperatureAfter cooling to ambient temperature
  3. customthe bulk of the THF was removed in vacuo
  4. customresulting in the formation of a precipitate
  5. filtrationThis mixture was filtered
  6. filtrationthrough filter paper
  7. washwashed with a minimal amount of water
  8. waitAfter placing under a strong vacuum for a few hours

Sources & evidence

ORD record
ord-f3e70efe234049a3989da342ebf5f18e
Source dataset
uspto-grants-2013_02
Patent number
US08372859B2

Reaction notes

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