Potassium Hydroxide → HCID 11170987, compound

HRID 1173760Notes

Reaction equation

HRID 1173760 reaction equation
Cl[C@H:2]([C@H:8]([OH:12])[CH2:9][CH2:10][CH3:11])[C:3]([O:5]CC)=[O:4].[O-]CC.[Na+].C(O)C.[OH-].[K+]>C(O)C>[CH2:9]([C@H:8]1[O:12][C@@H:2]1[C:3]([OH:5])=[O:4])[CH2:10][CH3:11]

Participants

5

Conditions

Temperature
5 °C

Procedure

Ethyl (2R,3R)-2-chloro-3-hydroxyhexanoate (5.0 g, 22 mmol) and ethanol (15 ml) were mixed, and the mixture was cooled to 5° C. To the mixture, 20% sodium ethoxide/ethanol solution (8.3 g, 24 mmol) was gradually added. The mixture was stirred at room temperature for 1 hour. The precipitated inorganic salt was separated by filtration. Potassium hydroxide (1.24 g, 24 mmol) was added to the filtrate, and the mixture was stirred at room temperature for 14 hours. The solvent was evaporated away under reduced pressure, and water (15 ml) was added. The pH was adjusted to 1.8 with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate (20 ml). The solvent was evaporated away under reduced pressure to obtain the title compound (2.33 g, yield: 65%).

Workup

  1. customThe precipitated inorganic salt was separated by filtration
  2. stirringthe mixture was stirred at room temperature for 14 hours
  3. customThe solvent was evaporated away under reduced pressure, and water (15 ml)
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate (20 ml)
  6. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-243f306a234245368c91339a1bc55432
Source dataset
uspto-grants-2010_11
Patent number
US07834190B2

Reaction notes

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