HCID 9865661, compound → HCID 9951222, compound

HRID 1589698Notes

Reaction equation

HRID 1589698 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:29])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH3:28])([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=1)[CH2:9][CH2:8]2)(=[O:3])[CH3:2].[H][H]>CO.C1C=CC=CC=1.C(OCC)(=O)C.[Pd]>[C:1]([O:4][C:5]1[C:6]([CH3:29])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=1)([CH3:28])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 9865661HCID 9865661, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9951222HCID 9951222, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 241BenzeneSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

24.3 g of 6-acetoxy-2,5,7,8-tetramethyl-2-(4-nitrophenoxymethyl)chroman were dissolved in a mixture of 200 ml of methanol and 20 ml of benzene and reacted for 3 hours under a hydrogen pressure of 45-55 lb/sq. inch (3.1-3.8 bars), using Pearl's hydrogen adding apparatus, in the presence of 7 g of 10% w/w palladium-on-carbon. The palladium-on-carbon was removed by filtration from the reaction mixture and washed with a mixture of 600 ml of acetone and 60 ml of concentrated hydrochloric acid. The filtrate and the washings were combined and the mixture was neutralized with sodium bicarbonate. The solvent was then distilled off, and the crude crystals obtained were dissolved in ethyl acetate. The ethyl acetate solution was washed with water and dried over anhydrous sodium sulfate. The ethyl acetate was then distilled from the extract, and the crude substance obtained was washed with a 1:1 by volume mixture of benzene and cyclohexane, giving the desired 6-acetoxy-2-(4-aminophenoxymethyl)-2,5,7,8-tetramethylchroman, melting at 138°-140° C.

Workup

  1. customreacted for 3 hours under a hydrogen pressure of 45-55 lb/sq
  2. customThe palladium-on-carbon was removed by filtration from the reaction mixture
  3. washwashed with a mixture of 600 ml of acetone and 60 ml of concentrated hydrochloric acid
  4. distillationThe solvent was then distilled off
  5. customthe crude crystals obtained
  6. washThe ethyl acetate solution was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe ethyl acetate was then distilled from the extract
  9. customthe crude substance obtained
  10. washwas washed with a 1:1 by volume mixture of benzene and cyclohexane

Sources & evidence

ORD record
ord-0118b5420d0a4cd0ba621e3e1447acae
Source dataset
uspto-grants-1986_02
Patent number
US04572912

Reaction notes

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