HCID 70045225, compound → HCID 19610505, compound

HRID 977017Notes

Reaction equation

HRID 977017 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:13]([O:15]CC1C=CC=CC=1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH:23]=[CH:24][C:25]=1[O:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:13]([OH:15])=[O:14])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 70045225HCID 70045225, compound

Product 1

HCID 19610505HCID 19610505, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of a solution of the product of step (b) (34.6 g) in ethyl acetate (600 ml) and 10% palladium/carbon (3 g) was stirred under an atmosphere of hydrogen for 5 hours at ambient temperature. The mixture was filtered through a pad of kieselguhr and the solvent was removed by evaporation to give a solid residue which was crystallised from ethyl acetate/hexane to give 3,4-di-t-butoxycarbonylmethoxybenzoic acid; m.p. 118°-120° C.; NMR Spectrum (d6 -DMSO) 1.41 (s, 18H), 4.7 (s, 2H), 4.76 (s, 2H), 6.95 (d, 1H), 7.39 (m, 1H), 7.55 (dd, 1H); Microanalysis found: C, 59.5; H, 6.8%; C19H26O8 requires C, 59.7; H, 6.9%.

Workup

  1. filtrationThe mixture was filtered through a pad of kieselguhr
  2. customthe solvent was removed by evaporation
  3. customto give a solid residue which
  4. customwas crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d4583e22d2554400b73148dcfd8e2313
Source dataset
uspto-grants-1997_03
Patent number
US05612373

Reaction notes

Loading…