Sulfuric Acid → Benzyl Alcohol

HRID 1614426Notes

Reaction equation

HRID 1614426 reaction equation
CCOCCOCCO.[BH4-].[Na+].[CH3:12][N:13]([CH3:22])[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][N:13]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:22].[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 11916N,N-DimethylbenzamideHCID 4311764Sodium borohydride

Product 2

HCID 244Benzyl AlcoholHCID 7681N,N-Dimethylbenzylamine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
120 °C

Procedure

10.7 g (0.08 mole) of ethyl carbitol was added dropwise to a mixture consisting of 1.5 g (0.04 mole) of sodium borohydride and 15 ml of xylene at 120° C. for 1.5 hours. The mixture was agitated at 120° C. for one hour. A mixture consisting of 3 g (0.02 mole) of N,N-dimethyl benzamide and 10 ml of xylene was added dropwise to the mixture over 0.5 hours. Subsequently, the resulting mixture was agitated at 120° C. for 20 hours. After cooling to room temperature, the mixture was neutralized with dilute sulfuric acid. As a result, N,N-dimethylbenzylamine was obtained in 51% yield and benzyl alcohol in 47% yield, respectively.

Workup

  1. additionwas added dropwise to the mixture over 0.5 hours
  2. stirringSubsequently, the resulting mixture was agitated at 120° C. for 20 hours
  3. temperatureAfter cooling to room temperature

Sources & evidence

ORD record
ord-6838703af3fb40f2951a1fec139271e7
Source dataset
uspto-grants-1993_03
Patent number
US05196601

Reaction notes

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