Hydrochloric Acid → HCID 89581007, compound

HRID 1501057Notes

Reaction equation

HRID 1501057 reaction equation
[O:1]([CH:8]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=[O:16])=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.CO.Cl>O>[O:1]([CH:8]([C:11]1[CH:12]=[CH:13][C:14]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=1)[CH2:9][CH3:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 89580813HCID 89580813, compound

Product 1

HCID 89581007HCID 89581007, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 4-(1-phenoxypropyl)benzoate (683 mg, 2.5 mmol) lithium hydroxide monohydrate (531 mg, 12.6 mmol), tetrahydrofuran (12 mL), methanol (4 mL) and water (4 mL) was stirred at 20° C. for 4 hours. The mixture was neutralized to pH to 1 with concentrated hydrochloric acid and then extracted with ethyl acetate (20 mL×3). The combined organic phase was separated, dried over sodium sulfate, and then filtered. The filtrate was concentrated in vacuo to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2:1) to give 4-(1-phenoxypropyl)benzoic acid as a white solid (640 mg, 100%). LRMS (M+H)− m/z: calcd 256.11. found 256.

Workup

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

Sources & evidence

ORD record
ord-c78cdcb7c97246298cb1cc99db3eda2d
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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