Ethanol → HCID 13020610, compound

HRID 1680880Notes

Reaction equation

HRID 1680880 reaction equation
Cl.[CH3:2][C:3]([NH:14][CH2:15][CH:16]([OH:31])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH2:24]C1C=CC=CC=1)([CH3:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.C(O)C.C([O-])(=O)C([O-])=O.C(O)(=O)C(O)=O>[H][H].[C].[Pd]>[CH3:13][C:3]([NH:14][CH2:15][CH:16]([OH:31])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])([CH3:2])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 971Oxalic AcidHCID 71081OxalateHCID 23454842HCID 23454842, compound

Product 1

HCID 13020610HCID 13020610, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

A mixture of 442 mg of α-[(α,α-dimethyl-4-methoxyphenethylamino)methyl]-2-benzyloxybenzylalcohol hydrochloride, 250 mg of 10% palladium-carbon and 25 ml of 95% aqueous ethanol is shaken at room temperature in hydrogen gas atmosphere under atmospheric pressure. After the uptake of hydrogen is completed, insoluble materials are removed by filtration. The filtrate is evaporated to remove the solvent. The residue (colorless oil) is alkalized with an aqueous ammonia solution, whereby 300 mg of a pale yellow oil are obtained. Said oil is converted into its oxalate by using 45 mg of oxalic acid, and the oxalate is recrystallized from 95% aqueous methanol. 243 mg of α-[(α,α-dimethyl-4-methoxyphenethylamino)methyl]-2-hydroxybenzylalcohol 1/2 oxalate are thereby obtained as colorless needles.

Workup

  1. custominsoluble materials are removed by filtration
  2. customThe filtrate is evaporated
  3. customto remove the solvent
  4. customare obtained
  5. customthe oxalate is recrystallized from 95% aqueous methanol

Sources & evidence

ORD record
ord-b0a7efe5bda54ff08859fc9d8a3e95f8
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

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