Sulfuric Acid → 4-tert-Butylcyclohexanol

HRID 1614420Notes

Reaction equation

HRID 1614420 reaction equation
C(OCCOCCO)C.[BH4-].[Na+].[C:12]([CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13].S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[C:12]([CH:16]1[CH2:17][CH2:18][CH:19]([OH:22])[CH2:20][CH2:21]1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 73924-tert-ButylcyclohexanoneHCID 8146Diethylene Glycol Monoethyl EtherHCID 4311764Sodium borohydride

Product 1

HCID 73914-tert-Butylcyclohexanol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
95 °C

Procedure

A mixture consisting of 0.52 g (0.0039 mole) of diethylene glycol monoethyl ether and 5 ml of xylene was added dropwise to a mixture consisting of 0.65 g (0.017 mole) of sodium borohydride, 10 ml of xylene and 10 g (0.065 mole) of 4-t-butylcyclohexanone at 95° C. over 30 minutes while agitating the mixture. Subsequently, the mixture was agitated for one hour while maintaining it at 95° C. Next, after the mixture was cooled to room temperature, it was neutralized with dilute sulfuric acid. As a result, 4-t-butylcyclohexanol was quantitatively obtained.

Workup

  1. additionwas added dropwise to a mixture
  2. stirringSubsequently, the mixture was agitated for one hour
  3. temperatureNext, after the mixture was cooled to room temperature

Sources & evidence

ORD record
ord-eb87045ad1924a14af555fed13eb50eb
Source dataset
uspto-grants-1993_03
Patent number
US05196601

Reaction notes

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