Hydrochloric Acid → Methyl 4-(phenoxymethyl)benzoic acid

HRID 1501004Notes

Reaction equation

HRID 1501004 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Li+].O1CCCC1.Cl>O.CO>[CH3:1][C:2]1[CH:11]=[C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 89581027Methyl 2-methyl-4-(phenoxymethyl)benzoate

Product 1

HCID 67601994Methyl 4-(phenoxymethyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-methyl-4-(phenoxymethyl)benzoate (66 mg, 0.26 mmol), lithium hydroxide (54 mg, 1.29 mmol), tetrahydrofuran (6 mL), methanol (2 mL), and water (2 mL) were stirred at room temperature for 12 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 2-methyl-4-(phenoxymethyl)benzoic acid used in next step without further purification (42 mg, 67%). LRMS (M+H)− m/z: calcd 242.09. found 242.

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

Sources & evidence

ORD record
ord-07d67d1b78be434186555c3cfea65a0c
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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