Benzyl Alcohol → Methyl 3-[4-(benzyloxy)phenyl]propanoate

HRID 1678566Notes

Reaction equation

HRID 1678566 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[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.O>[C:15]1([CH2:14][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 11776TriphenylphosphineHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl esterHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 525519Methyl 3-[4-(benzyloxy)phenyl]propanoateYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ice-cooled methyl 4-hydroxybenzenepropanoate (0.70 g, 3.9 mmol), benzyl alcohol (0.48 mL, 4.7 mmol) and triphenylphosphine (1.2 g, 4.7 mmol) in tetrahydrofuran (5 mL) was added dropwise diethyl azodicarboxylate (0.73 mL, 4.7 mmol), and the mixture was stirred for 2 hours with ice cooling. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=17:3) to give the title compound (0.62 g, yield 59%) as powders.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=17:3)

Sources & evidence

ORD record
ord-94811af0a74842db852b11662b014c8a
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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