Sulfuric Acid → 1-Decanol

HRID 1614423Notes

Reaction equation

HRID 1614423 reaction equation
C(OCCOCCO)C.[BH4-].[Na+].[O:12](C)[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=O.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[CH2:13]([OH:12])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8050Methyl DecanoateHCID 8146Diethylene Glycol Monoethyl EtherHCID 4311764Sodium borohydride

Product 1

HCID 81741-DecanolYield 97%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

11.2 g (0.083 mole) of diethylene glycol monoethyl 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 90° C. over two hours while agitating the mixture. Subsequently, the mixture was agitated at the same temperature for 2.5 hours. After cooling to room temperature, the mixture was neutralized with dilute sulfuric acid. As a result, n-decanol was obtained in 97% yield.

Workup

  1. stirringSubsequently, the mixture was agitated at the same temperature for 2.5 hours

Sources & evidence

ORD record
ord-b8f2401ee8bd44b588216e090cc0cd36
Source dataset
uspto-grants-1993_03
Patent number
US05196601

Reaction notes

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