Lithium Hydroxide → HCID 59444079, compound

HRID 1968987Notes

Reaction equation

HRID 1968987 reaction equation
[CH3:1][C:2]1([C:12]([O:14]CC2C=CC=CC=2)=[O:13])[CH2:7][CH2:6][CH:5]([O:8][CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1.O1CCCC1.[OH-].[Li+]>O>[CH3:1][C:2]1([C:12]([OH:14])=[O:13])[CH2:7][CH2:6][CH:5]([O:8][CH:9]([CH3:11])[CH3:10])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59444101HCID 59444101, compound

Product 1

HCID 59444079HCID 59444079, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenylmethyl 1-methyl-4-[(1-methylethyl)oxy]cyclohexanecarboxylate (D108) (2.3 g, 7.92 mmol) was suspended in water (30 mL) and tetrahydrofuran (THF) (10 mL) along with lithium hydroxide (0.759 g, 31.7 mmol). The resulting solution was warmed to reflux overnight, TLC (SiO2 10% EtOAc/is-hex) showed some of more polar SM present but none of less polar SM. Reaction cooled and extracted with ether (2×20 mL) to remove unhydrolysed SM. Aqueous layer acidified with 2 N HCl (acid to pH stick) and extracted into DCM (2×15 mL). DCM layers combined and dried over MgSO4, filtered and solvent removed under reduced pressure. NMR confirmed 1-methyl-4-[(1-methylethyl)oxy]cyclohexanecarboxylic acid (1.13 g, 5.64 mmol, 71.2% yield) as a mixture of cis and trans isomers. As suspected from the TLC one of the isomers, suspected to be the trans (ether:carboxylate) had hydrolysed faster. This resulted in a ˜2:1 ratio of the acids.

Workup

  1. temperatureThe resulting solution was warmed
  2. temperatureto reflux overnight
  3. customReaction
  4. temperaturecooled
  5. extractionextracted with ether (2×20 mL)
  6. customto remove unhydrolysed SM
  7. extractionextracted into DCM (2×15 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customsolvent removed under reduced pressure

Sources & evidence

ORD record
ord-f9e51bc291d04f37b64a3bbf9de69522
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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