Benzyl Alcohol → HCID 20434082, compound

HRID 1154617Notes

Reaction equation

HRID 1154617 reaction equation
CC(N=C(OC)C(C1C=CC=CC=1)=O)CC1C=CC(OC)=CC=1.[BH4-].[Na+].[CH3:26][CH:27]([NH:37][CH2:38][CH:39]([OH:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[O:46][CH3:47])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1.C(O)C1C=CC=CC=1.[ClH:57]>C(O)C>[ClH:57].[CH3:26][CH:27]([NH:37][CH2:38][CH:39]([OH:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[O:46][CH3:47])[CH2:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 313Hydrochloric Acid2×HCID 4311764Sodium borohydrideHCID 13365127HCID 13365127, compoundHCID 20434109alpha-(alpha-Methyl-4-methoxyphenethylimino)-2-methoxyacetophenone

Product 1

HCID 20434082HCID 20434082, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the α-(α-methyl-4-methoxyphenethylimino)-2-methoxyacetophenone solution, 0.76 g of sodium borohydride and 12 ml of ethanol is treated in the same manner as described in Example 1-(3), whereby α-[(α-methyl-4-methoxyphenethylamino)methyl]-2-methoxybenzylalcohol [the mixture of two diastereoisomers] is obtained as a crude oil. Said benzylalcohol [i.e., the mixture of two diastereoisomers] is treated with ethanolic hydrogen chloride to convert it into its hydrochloride, and the hydrochloride is recrystallized from a mixture of ethanol and ether. The crystalline precipitates are collected by filtration (the filtrate is hereinafter referred to as "mother liquor"). 1.85 g of α-[(α-methyl-4-methoxyphenethylamino)methyl]-2-methoxybenzylalcohol hydrochloride [the diastereoisomer of M.p. 161°-163° C.] is thereby obtained.

Workup

  1. additionis treated in the same manner
  2. customis obtained as a crude oil
  3. additionthe mixture of two diastereoisomers]
  4. customthe hydrochloride is recrystallized from a mixture of ethanol and ether
  5. customThe crystalline precipitates
  6. filtrationare collected by filtration (the filtrate

Sources & evidence

ORD record
ord-0f0b46c074a44686bb6cef8e47fd2df2
Source dataset
uspto-grants-1984_12
Patent number
US04490392

Reaction notes

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