Hydrochloric Acid → HCID 57617617, compound

HRID 1960029Notes

Reaction equation

HRID 1960029 reaction equation
[OH-].[K+].[CH2:3]([O:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH:15]([C:18](=[O:26])[CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])[CH2:14][CH2:13]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CCO>[CH2:3]([O:10][CH2:11][CH:12]1[CH2:13][CH2:14][CH:15]([C:18](=[O:26])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:16][CH2:17]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 57617593HCID 57617593, compound

Product 1

HCID 57617617HCID 57617617, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Potassium hydroxide (17.0 g, 0.30 mol) is added to EtOH (300 mL) solution of ethyl 4-[4-(benzyloxymethyl)cyclohexyl]-4-oxobutyrate (cis/trans=1/1, 33.0 g, 0.10 mol), and the mixture is stirred at 85° C. for 2 hours. After cooling to 0° C., 5N HCl is added to the mixture (to reach pH 2-3), the mixture is concentrated to remove ethanol. The crude mixture is extracted with EtOAc. The water layer is extracted with EtOAc, and the combined organic layer is washed with water and brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford crude 4-[4-(benzyloxymethyl)cyclohexyl]-4-oxobutyric acid (cis/trans=ca. 1/6). The mixture of ether-hexane (ca. 1:4, 120 mL) is added to the resulting solid and sonicated. The crystal is collected by filtration, washed with small amount of ether-hexane (1:4) and dried to give trans-4-[4-(benzyloxymethyl)cyclohexyl]-4-oxobutyric acid as a pale yellow solid.

Workup

  1. temperatureAfter cooling to 0° C.
  2. concentrationthe mixture is concentrated
  3. customto remove ethanol
  4. extractionThe crude mixture is extracted with EtOAc
  5. extractionThe water layer is extracted with EtOAc
  6. washthe combined organic layer is washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f861eb9427d4a7ea1a8378b6087811f
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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