Triphenylphosphine → 4-(1-Tert-butoxy-2-propoxy)-3-chlorobenzoic acid methyl ester

HRID 2196482Notes

Reaction equation

HRID 2196482 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([Cl:11])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:44]([O:48][CH2:49][CH:50](O)[CH3:51])([CH3:47])([CH3:46])[CH3:45]>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:50]([CH3:51])[CH2:49][O:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[C:6]([Cl:11])[CH:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 926291-tert-Butoxy-2-propanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 671137004-(1-Tert-butoxy-2-propoxy)-3-chlorobenzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.5 g of 3-chloro-4-hydroxybenzoic acid methyl ester in 20 ml of THF, 1.8 ml of 1-tert-butoxy-2-propanol, 3.16 g of triphenylphosphine, and 1.9 ml of diethylazodicarboxylate were added, and the mixture was stirred at room temperature for 1 hour. After evaporation of the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=100:1˜5:1) to obtain 2.3 g of 4-(1-tert-butoxy-2-propoxy)-3-chlorobenzoic acid methyl ester.

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (eluent: hexane-EtOAc=100:1˜5:1)

Sources & evidence

ORD record
ord-76f06a9e46bd401f8065341389bfc696
Source dataset
uspto-grants-2012_12
Patent number
US08338429B2

Reaction notes

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