(+/-)-6-Benzyloxy-2-methoxy-2-methylchroman → (+/-)-6-Hydroxy-2-methoxy-2-methylchroman

HRID 268416Notes

Reaction equation

HRID 268416 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([O:20][CH3:21])([CH3:19])[CH2:13][CH2:12]2)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[O:15][C:14]([O:20][CH3:21])([CH3:19])[CH2:13][CH2:12]2

Participants

5

Reactant 2

HCID 21432288(+/-)-6-Benzyloxy-2-methoxy-2-methylchromanHCID 178418361HCID 178418361, compound

Product 1

HCID 14415693(+/-)-6-Hydroxy-2-methoxy-2-methylchroman

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the (±)-6-benzyloxy-2-methoxy-2-methylchroman prepared in Example 45 in 250 ml. of ethanol was added 2.5 g. of 10% palladium on carbon catalyst, and the resulting mixture was hydrogenated at atmospheric pressure and room temperature. After 9 hours, the uptake of hydrogen (3100 ml.) had ceased. The catalyst was removed by filtration and the filtrates were stripped of solvent at reduced pressure. Crystallization of the solid residue from ether-30°-60° petroleum ether gave (±)-6-hydroxy-2-methoxy-2-methylchroman as white needles, m.p. 128°-130°.

Workup

  1. customwas hydrogenated at atmospheric pressure and room temperature
  2. customThe catalyst was removed by filtration
  3. customCrystallization of the solid residue from ether-30°-60° petroleum ether

Sources & evidence

ORD record
ord-108b000ed4ab442aa69b69faa81364eb
Source dataset
uspto-grants-1976_03
Patent number
US03947473

Reaction notes

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