Toluene → 6-Methacryloyl-2-oxohexahydro-3,5-methano-2h-cyclopenta[b]furan-7-carboxylic acid

HRID 558049Notes

Reaction equation

HRID 558049 reaction equation
[C:1]([CH:6]1[CH:10]2[O:11][C:12](=[O:22])[CH:13]3[CH:14]([C:15]([O:17]C(C)(C)C)=[O:16])[CH:7]1[CH2:8][CH:9]23)(=[O:5])[C:2]([CH3:4])=[CH2:3].C1(C)C=CC=CC=1.C(OC(C)(C)C)=O>C(O)=O>[C:1]([CH:6]1[CH:10]2[O:11][C:12](=[O:22])[CH:13]3[CH:14]([C:15]([OH:17])=[O:16])[CH:7]1[CH2:8][CH:9]23)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 61207tert-Butyl FormateHCID 67000815Tert-butyl 6-methacryloyl-2-oxohexahydro-3,5-methano-2h-cyclopenta[b]furan-7-carboxylate

Product 1

HCID 670009756-Methacryloyl-2-oxohexahydro-3,5-methano-2h-cyclopenta[b]furan-7-carboxylic acidYield 90%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent2×

Procedure

In 80 g of formic acid was dissolved 20.0 g of the methacrylate obtained in Example 1-1-1. The solution was stirred at room temperature overnight. Toluene was added to the reaction solution, from which formic acid and tert-butyl formate were azeotroped off. Recrystallization from hexane yielded 14.7 g of the target compound (yield 89%).

Workup

  1. customwere azeotroped off
  2. customRecrystallization from hexane

Sources & evidence

ORD record
ord-0f0127ec0e874036a27aee9e6081cc9c
Source dataset
uspto-grants-2011_11
Patent number
US08062831B2

Reaction notes

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