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Acetic Anhydride → Lactic Acid

HRID 365239
Notes
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Reaction equation

HRID 365239 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]([OH:9])[C:6]([OH:8])=[O:7].C(O)(=O)[C@H](C)O.C(OC(=O)C)(=O)C>O>[C:6]([OH:8])(=[O:7])[CH:5]([CH3:4])[OH:9].[OH:9][CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[C:6]([OH:8])=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 998242-Hydroxyhexanoic acidHCID 107689L-Lactic Acid

Product 2

HCID 612Lactic AcidHCID 998242-Hydroxyhexanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

DL-2-Hydroxycaproic acid (1.00 gram, 0.0076 mole), and L-lactic acid (4.5 grams of a nominally 85% solution in water; 0.043 mole) were placed in a reaction flask equipped with a distillation head and mechanical stirrer. The flask was heated at 110° C. for 6 hours under low vacuum (aspirator) while water was removed. The temperature was then raised to 140° C. for 6 hours. Acetic anhydride (5.16 grams; 0.0506 moles) was added to the polymer, followed by heating at 80° C. for 14 hours. Excess acetic anhydride and acetic acid were distilled off under low vacuum. Tetrahydrofuran/water (15 mL of 85/15; volume/volume) was added with stirring and heating at 60° C. for 0.5 hour. The bulk of the solvent was removed by vacuum distillation on a rotary evaporator. The resulting crude product was dissolved in chloroform (20 mL). The chloroform solution was washed twice with millipore water (5 mL) and then dried with MgSO4. The mixture was filtered through a "d" fritted glass funnel and the solvent distilled from the polymer by rotary evaporation. Final traces of solvents were removed under high vacuum (0.4 mm Hg) on a Kugelrohr apparatus at 120° C. to provide acetyl-poly(DL-2-hydroxycaproic-co-L-lactic acid) with n=7.5 for lactic acid and 1.4 for hydroxycaproic acid, Mn=763, and Mw=1044 (by GPC).

Workup

  1. custom0.043 mole) were placed in a reaction flask
  2. customequipped with a distillation head and mechanical stirrer
  3. customwas removed
  4. temperatureby heating at 80° C. for 14 hours
  5. distillationExcess acetic anhydride and acetic acid were distilled off under low vacuum
  6. additionTetrahydrofuran/water (15 mL of 85/15; volume/volume) was added
  7. temperatureheating at 60° C. for 0.5 hour
  8. customThe bulk of the solvent was removed by vacuum distillation on a rotary evaporator
  9. dissolutionThe resulting crude product was dissolved in chloroform (20 mL)
  10. washThe chloroform solution was washed twice with millipore water (5 mL)
  11. dry with materialdried with MgSO4
  12. filtrationThe mixture was filtered through a "d" fritted glass funnel
  13. distillationthe solvent distilled from the polymer by rotary evaporation
  14. customFinal traces of solvents were removed under high vacuum (0.4 mm Hg) on a Kugelrohr apparatus at 120° C.

Sources & evidence

ORD record
ord-4927d39a35154dfa9d6b9525e9cbaaf9
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06126919

Reaction notes

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