Benzyl Alcohol → 2-Benzyloxy-3-methoxybenzoic acid methyl ester

HRID 51922Notes

Reaction equation

HRID 51922 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=1[OH:13].[CH2:14](O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[C:4]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 80651Methyl 3-methoxysalicylateHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 698916402-Benzyloxy-3-methoxybenzoic acid methyl esterYield 58.2%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-methoxysalicylate (1.0 g, 5.49 mmol) in 5 ml tetrahydrofuran and 5 ml dimethylformamide was added sequentially at room temperature, benzyl alcohol (0.71 ml, 6.86 mmol), triphenylphosphine (2.16 g, 8.23 mmol) and diethyl azodicarboxylate (1.3 ml, 8.23 mmol). The reaction solution was stirred at room temperature overnight, then ethyl acetate was added and the resulting solution was washed sequentially with water and brine. The ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was triturated with diethyl ether and filtered to remove triphenylphosphine oxide. The ether solution was concentrated to dryness in vacuo and the residue was purified by column chromatography on silica gel, eluting with 95:5 hexane/ethyl acetate, yielding the title compound as an oil (870 mg 58% yield).

Workup

  1. washthe resulting solution was washed sequentially with water and brine
  2. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness in vacuo
  4. customThe residue was triturated with diethyl ether
  5. filtrationfiltered
  6. customto remove triphenylphosphine oxide
  7. concentrationThe ether solution was concentrated to dryness in vacuo
  8. customthe residue was purified by column chromatography on silica gel
  9. washeluting with 95:5 hexane/ethyl acetate

Sources & evidence

ORD record
ord-8a9bc6c4806c43a6aaad164dbf6a2a4e
Source dataset
uspto-grants-2004_03
Patent number
US06713489B2

Reaction notes

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