Methanol → HCID 19822260, compound

HRID 1030404Notes

Reaction equation

HRID 1030404 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:36])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-])=O)=[CH:29][CH:28]=1)([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].CO.[H][H]>[Pd].C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([CH3:36])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]([NH2:33])=[CH:31][CH:32]=1)([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 19822253HCID 19822253, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19822260HCID 19822260, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 241BenzeneSolvent

Procedure

Using Paar's hydrogenation apparatus, a mixture of 4 g of 6-acetoxy-5,7,8-trimethyl-2-(4-nitrophenoxymethyl)-2-octylchroman (prepared as described in Preparation 16), 0.8 g of 10% w/w palladium-on-carbon, 30 ml of methanol and 10 ml of benzene was stirred for 5 hours under 3-5 atmospheres (about 3-5 bars) pressure or hydrogen. The catalyst was filtered off, and the filtrate was condensed by evaporation under reduced pressure. The crystals thus obtained were washed with hexane to give the title compound, melting at 112°-114° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customcondensed
  3. customby evaporation under reduced pressure
  4. customThe crystals thus obtained
  5. washwere washed with hexane

Sources & evidence

ORD record
ord-997a75bd7e514d3b9a0a923c804c4e2b
Source dataset
uspto-grants-1992_04
Patent number
US05104888

Reaction notes

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