Sulfuric Acid → Benzyl Alcohol

HRID 1614427Notes

Reaction equation

HRID 1614427 reaction equation
CCOCCOCCO.[BH4-].[Na+].[CH3:12][NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[CH3:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8146Diethylene Glycol Monoethyl EtherHCID 11954N-MethylbenzamideHCID 4311764Sodium borohydride

Product 2

HCID 244Benzyl AlcoholHCID 7669N-Methylbenzylamine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

29.8 g (0.222 mole) of ethyl carbitol was added dropwise to a mixture consisting of 2.8 g (0.074 mole) of sodium borohydride, 5 g (0.037 mole) of N-methyl benzamide and 25 ml of xylene at 120° C. over two hours. Subsequently, the mixture was agitated at the same temperature for 40 hours. After cooling to room temperature, the mixture was neutralized with dilute sulfuric acid. As a result, N-methyl benzylamine was obtained in 67.5% yield and benzyl alcohol in 7.7% yield, respectively. 23.6% of N-methyl benzamide was remained unreactive.

Sources & evidence

ORD record
ord-ad65dd5e969544989c9e38216d1a3295
Source dataset
uspto-grants-1993_03
Patent number
US05196601

Reaction notes

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