Sulfuric Acid → 1-Decanol

HRID 1614424Notes

Reaction equation

HRID 1614424 reaction equation
C(OCCOCCO)CCC.[BH4-].[Na+].[O:14](C)[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=O.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[CH2:15]([OH:14])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8050Methyl DecanoateHCID 8177Diethylene Glycol Monobutyl EtherHCID 4311764Sodium borohydride

Product 1

HCID 81741-DecanolYield 98%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

13.5 g (0.083 mole) of diethylene glycol monobutyl ether was added dropwise to a mixture consisting of 1.6 g (0.042 mole) of sodium borohydride, 10 ml of xylene and 5 g (0.027 mole) of methyl caprate at 95° C. over two hours while agitating the mixture. Subsequently, the mixture was agitated at the same temperature for two hours. After cooling to room temperature, the mixture was neutralized with dilute sulfuric acid. As a result, n-decanol was obtained in 98% yield.

Workup

  1. stirringSubsequently, the mixture was agitated at the same temperature for two hours

Sources & evidence

ORD record
ord-ec829c3661a342869b8e8ecafcf0b603
Source dataset
uspto-grants-1993_03
Patent number
US05196601

Reaction notes

Loading…