1,10-Undecanediol → 4-(Hydroxymethyl)cyclohexan-1-one

HRID 2290977Notes

Reaction equation

HRID 2290977 reaction equation
C(O)CCCCCCCCC(O)C.[OH:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18][CH2:17]1>C(O)(=O)C>[OH:14][CH2:15][CH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 109762551,10-UndecanediolHCID 12892866Rac-(1s,4s)-4-(hydroxymethyl)cyclohexanol

Product 1

HCID 128928674-(Hydroxymethyl)cyclohexan-1-oneYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
55 °C

Procedure

To acetic acid in which Ce (IV)/PFCP (50 mg, 0.027 mmole) and 200 mg of NaBrO3 were dispersed and dissolved, 1.0 mmole of 1,10-undecane diol and 1.0 mmole of 4-hydroxymethyl cyclohexanol were added, respectively. The reaction mixture was heated for three hours at 55° C. and the product was purified with a column chromatography to yield 154 mg (82% yield) of 10-undecane-1-ol and 93 mg (73% yield) of 4-hydroxymethyl cyclohexanone.

Workup

  1. dissolutiondissolved
  2. customthe product was purified with a column chromatography

Sources & evidence

ORD record
ord-f5c3815be4c94793a69f03df51be1fd2
Source dataset
uspto-grants-1986_10
Patent number
US04618724

Reaction notes

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