Sulfuric Acid → 1-Decanol

HRID 1614425Notes

Reaction equation

HRID 1614425 reaction equation
C(OCCOCCOCCO)C.[BH4-].[Na+].[O:15](C)[C:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=O.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[CH2:16]([OH:15])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8050Methyl DecanoateHCID 8190Triethylene glycol monoethyl etherHCID 4311764Sodium borohydride

Product 1

HCID 81741-DecanolYield 99%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

14.8 g (0.083 mole) of triethylene 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 95° C. over two hours while agitating the mixture. Subsequently, the mixture was agitated at the same temperature for 1.5 hours. After cooling to room temperature, the mixture was neutralized with dilute sulfuric acid. As a result, n-decanol was obtained in 99% yield.

Workup

  1. stirringSubsequently, the mixture was agitated at the same temperature for 1.5 hours

Sources & evidence

ORD record
ord-b1428e94e0fb411ea1fc20d6b1347817
Source dataset
uspto-grants-1993_03
Patent number
US05196601

Reaction notes

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