Sodium Hydroxide → HCID 10910211, compound

HRID 862911Notes

Reaction equation

HRID 862911 reaction equation
[CH2:1]1[CH2:5][C:4]2([CH2:12][C:10](=[O:11])[O:9][C:7](=[O:8])[CH2:6]2)[CH2:3][CH2:2]1.BrBr.[OH-:15].[Na+]>>[O:8]=[C:7]1[CH2:6][C:4]2([CH2:3][CH2:2][CH2:1][CH2:5]2)[CH:12]([C:10]([OH:9])=[O:11])[O:15]1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24408Bromine2×HCID 79743Cyclopentane-1,1-diacetic anhydride

Product 1

HCID 10910211HCID 10910211, compound

Procedure

3,3-Tetramethylene glutaric anhydride (5 g, 30 mmol) was heated to 105° C. and irradiated with a sun lamp while bromine (2 ml, 38.7 mmol) was added dropwise. After the bromine color dispersed, the reaction was cooled to room temperature and 2.4M NaOH (50 ml) was added and the mixture was heated to reflux for 2 hours. The solution was cooled to room temperature and the pH was adjusted to pH 2 and stirred in a ice water bath for 0.5 hour. The precipitate (unreacted 3,3-tetrametylene glutaric acid) was filtered and discarded. The filtrate was extracted three times with ethyl acetate and the combined organics were washed with brine and dried over MgSO4. Evaporation yielded the title acid as a colorless oil, 5 g, 90%. NMR (CDCl3, 300 MHz) δ 7.95 (broad s, OH), 4.65 (s, 1, methine), 2.61 and 2.35 (ab, 2, methylene), 1.9-1.45 (m, 8, tertramethylene).

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 2 hours
  4. temperatureThe solution was cooled to room temperature
  5. filtrationThe precipitate (unreacted 3,3-tetrametylene glutaric acid) was filtered
  6. extractionThe filtrate was extracted three times with ethyl acetate
  7. washthe combined organics were washed with brine
  8. dry with materialdried over MgSO4
  9. customEvaporation

Sources & evidence

ORD record
ord-77c6cbd9a16540adb70ab922e5141d83
Source dataset
uspto-grants-1998_02
Patent number
US05719286

Reaction notes

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