Hydrochloric Acid → Methyl 5-(hydroxymethyl)-2-methoxybenzoate

HRID 2230608Notes

Reaction equation

HRID 2230608 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].O1CCCC1.O1CCCC1.B.Cl>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuran2×HCID 10856352Methyl 5-formyl-2-methoxybenzoate

Product 1

HCID 18465013Methyl 5-(hydroxymethyl)-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine methyl 2-methoxy-5-formylbenzoate (0.1 g, 0.5 mmol) and tetrahydrofuran (2 mL). Cool in an ice bath. Add a solution of borane tetrahydrofuran complex (0.17 mL, 1 M in tetrahydrofuran, 0.17 mmol). After 1.5 hours, again add a solution of borane tetrahydrofuran complex (0.17 mL, 1 M in tetrahydrofuran, 0.17 mmol). After 2 hours, add a 1 M aqueous solution of hydrochloric acid (2 mL) and stir. After 15 minutes, dilute the reaction mixture with ethyl acetate. Separates the layers, extract the aqueous layer three times with ethyl acetate and combine the organic layers. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give methyl 2-methoxy-5-hydroxymethylbenzoate: Rf=0.32 (silica gel, ethyl acetate).

Workup

  1. temperatureCool in an ice bath
  2. waitAfter 2 hours
  3. waitAfter 15 minutes
  4. extractionSeparates the layers, extract the aqueous layer three times with ethyl acetate
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-1453a4966177433784c49fa2096066e5
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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