Hydrochloric Acid → HCID 56998584, compound

HRID 1501073Notes

Reaction equation

HRID 1501073 reaction equation
[CH3:1][CH:2]([CH3:22])[CH2:3][CH:4]([C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O.[OH-].[Li+].O1CCCC1.Cl>O.CO>[CH3:1][CH:2]([CH3:22])[CH2:3][CH:4]([C:12]1[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=1)[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 89580867HCID 89580867, compound

Product 1

HCID 56998584HCID 56998584, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of methyl 4-(3-methyl-1-phenoxybutyl)benzoate (25 mg, 0.084 mmol), lithium hydroxide monohydrate (42 mg, 1 mmol), tetrahydrofuran (6 mL), methanol (2 mL) and water (2 mL) was stirred at 20° C. for 4 hours. The mixture was acidified to pH=1 with concentrated hydrochloric acid and then extracted with dichloromethane (10 mL×3). The combined organic phase was dried by sodium sulfate and filtered. The filtrate was concentrated in vacuo to give 4-(3-methyl-1-phenoxybutyl)benzoic acid (24 mg, 99%).

Workup

  1. extractionextracted with dichloromethane (10 mL×3)
  2. dry with materialThe combined organic phase was dried by sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-54fad69f02a1418397f97267417ebd03
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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