Potassium Hydroxide → HCID 59997883, compound

HRID 1717445Notes

Reaction equation

HRID 1717445 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)[O:25][C:26]=3[CH3:27])[CH2:15]2)[C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[K+]>C(O)(C)C.O>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C@@H:14]2[CH2:19][CH2:18][CH2:17][C@H:16]([O:20][CH2:21][C:22]3[N:23]=[C:24]([C:28]4[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=4)[O:25][C:26]=3[CH3:27])[CH2:15]2)[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58681962HCID 58681962, compound2×

Product 1

HCID 59997883HCID 59997883, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
95 °C

Procedure

from methyl methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)-cyclohexyloxymethyl]benzoate: 97.1 g (165 mmol) of methyl methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexyloxymethyl]benzoate are dissolved in a mixture of 640 ml of isopropanol and 80 ml of water. 47.7 g (809 mmol) of potassium hydroxide are added in portions. The reaction is stirred at 95° C. for 24 hours. Subsequently, the solvent is removed fully under reduced pressure and the residue is taken up in 800 ml of tert-butyl methyl ether and 800 ml of water. Addition of hydrochloric acid (2 M) acidifies the mixture. After phase separation, the organic phase is washed four times with 200 ml each time of water. The organic phase is concentrated under reduced pressure and the residue is stirred with a little diisopropyl ether. The solid is filtered and dried under reduced pressure. 2-methyl-6-[(1R,3S)-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)-cyclohexyloxymethyl]benzoic acid is obtained in 57% yield as a crystalline solid.

Workup

  1. customSubsequently, the solvent is removed fully under reduced pressure
  2. additionAddition of hydrochloric acid (2 M)
  3. customAfter phase separation
  4. washthe organic phase is washed four times with 200 ml each time of water
  5. concentrationThe organic phase is concentrated under reduced pressure
  6. stirringthe residue is stirred with a little diisopropyl ether
  7. filtrationThe solid is filtered
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-253f7d20622842aa94257b5a3478a1da
Source dataset
uspto-grants-2010_09
Patent number
US07803950B2

Reaction notes

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