Sulfuric Acid → 1-Decanol

HRID 1614422Notes

Reaction equation

HRID 1614422 reaction equation
C(OCCO)C.[BH4-].[Na+].[O:9](C)[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=O.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[CH2:10]([OH:9])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8050Methyl DecanoateHCID 8076Glycol monoethyl etherHCID 4311764Sodium borohydride

Product 1

HCID 81741-DecanolYield 90%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

7.5 g (0.083 mole) of ethylene 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 90% yield.

Workup

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

Sources & evidence

ORD record
ord-2512dfed603e407d8df8cce28b6bba44
Source dataset
uspto-grants-1993_03
Patent number
US05196601

Reaction notes

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