Methanol → HCID 89581171, compound

HRID 1501029Notes

Reaction equation

HRID 1501029 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([O:7][CH:8]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=2)[CH3:9])=[CH:3][CH:2]=1.O.[OH-].[Li+].O1CCCC1.CO>O>[C:1]1([CH3:20])[CH:2]=[CH:3][C:4]([O:7][CH:8]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=2)[CH3:9])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89581301HCID 89581301, compound

Product 1

HCID 89581171HCID 89581171, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 4-(1-(p-tolyloxy)ethyl)benzoate (50 mg, 0.19 mmol), lithium hydroxide monohydrate (39 mg, 0.92 mmol), tetrahydrofuran (6 mL), methanol (2 mL), and water (2 mL) were stirred at 20° C. for 12 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 4-(1-(p-tolyloxy)ethyl)benzoic acid used in next step without further purification (42 mg, 86%). LRMS (M+H)− m/z: calcd 256.11. found 256.

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

Sources & evidence

ORD record
ord-4cd9dd974f114bf8b8c54883f83c38f7
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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