Methanol → HCID 89580898, compound

HRID 1501053Notes

Reaction equation

HRID 1501053 reaction equation
[CH3:1][CH:2]([CH3:21])[CH:3]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=1)[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.[OH-].[Li+].O1CCCC1.CO>O>[CH3:1][CH:2]([CH3:21])[CH:3]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=1)[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89580956HCID 89580956, compound

Product 1

HCID 89580898HCID 89580898, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 4-(2-methyl-1-phenoxypropyl)benzoate (240 mg, 0.84 mmol), lithium hydroxide monohydrate (178 mg, 4.2 mmol), tetrahydrofuran (12 mL), methanol (4 mL) and water (4 mL) was stirred at 20° C. for 4 hours. The reaction mixture was concentrated, acidified with concentrated hydrochloric acid to pH=1, extracted with ethyl acetate (20 mL×3). The organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give 4-(2-methyl-1-phenoxypropyl)benzoic acid as a white solid (227 mg, 100%). LRMS (M+H)− m/z: calcd 268.15. found 268.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate (20 mL×3)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1e413034707e47998ab10b912adc8a53
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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