Tetrahydrofuran → 4-(4-Chlorophenyl)-4-(hydroxymethyl)cyclohexan-1-one

HRID 1576213Notes

Reaction equation

HRID 1576213 reaction equation
[C:1]([C:4]1([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)(O)=[O:2].O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[OH:2][CH2:1][C:4]1([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[CH2:5][CH2:6][C:7](=[O:10])[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 204534561-(4-CHLOROPHENYL)-4-OXOCYCLOHEXANECARBOXYLIc acid2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 215146584-(4-Chlorophenyl)-4-(hydroxymethyl)cyclohexan-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 19.26 g. (0.065 mole) of 4-carboxy-4-(4-chlorophenyl)cyclohexanone, ethylene ketal (prepared in Example 25) in 320 ml. of tetrahydrofuran is added to 5.9 g. (0.155 mole) of lithium aluminum hydride in 85 ml. of tetrahydrofuran. Following about 6 hours of heating at reflux, the mixture is cooled in ice and treated successively with 6 ml. of water, 6 ml. of 15% sodium hydroxide solution and 18 ml. of water. The resulting inorganic gel is collected on a filter and rinsed with ether. The combined filtrates are evaporated to dryness to give 19.23 g. (99% yield) of 4-hydroxymethyl-4-(4-chlorophenyl)cyclohexanone, ethylene ketal as an amorphous gum.

Workup

  1. temperatureof heating
  2. temperatureat reflux
  3. temperaturethe mixture is cooled in ice
  4. additiontreated successively with 6 ml
  5. customThe resulting inorganic gel is collected on
  6. filtrationa filter
  7. washrinsed with ether
  8. customThe combined filtrates are evaporated to dryness
  9. customto give 19.23 g

Sources & evidence

ORD record
ord-acd83e11b5a34fc08965651b2264f2db
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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