4-(Dimethoxy-phosphorylmethyl)-benzoic acid methyl ester → Methyl Benzoate

HRID 1836907Notes

Reaction equation

HRID 1836907 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7](CP(OC)(OC)=O)=[CH:6][CH:5]=1.CCC([O-])(C)C.[K+]>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 108011704-(Dimethoxy-phosphorylmethyl)-benzoic acid methyl esterHCID 23683543Potassium t-amylate

Product 1

HCID 7150Methyl Benzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2.0 g (6.6 mmol ) of 2,2,4,4,7,9,9-heptamethyl-3a,4,9,9a-tetrahydro-naphtho[2,3-d][1,3]-trans-dioxole-6-carbaldehyde and 2.2 g (8.6 mmol) of 4-(Dimethoxy-phosphorylmethyl)-benzoic acid methyl ester in 50 ml of toluene at 0° was added 5.6 ml of 1.7 M (8.6 mmol) of potassium tert-pentylate in toluene. After 1.5 h, poured into brine, extracted with ethyl acetate, dried over sodium sulfate and adsorbed onto silica gel. Purified by flash chromatography (gradient elution: hexane-2% ethyl acetae/hexane) to give 2.5 g (87%) of 4-[(E)-2-(2,2,4,4,7,9,9)-heptamethyl-3a,4,9,9a-tetrahydro-naphtho[2,3d][1,3]-trans-dioxol-6-yl)-vinyl]-benzoic acid methyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. customPurified by flash chromatography (gradient elution: hexane-2% ethyl acetae/hexane)

Sources & evidence

ORD record
ord-c3e4309cd44b426b9c14c043b59b1bbe
Source dataset
uspto-grants-2004_08
Patent number
US06777418B2

Reaction notes

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