Tetrahydrofuran → 4-(Hydroxymethyl)-4-(naphthalen-1-yl)cyclohexan-1-one

HRID 1576215Notes

Reaction equation

HRID 1576215 reaction equation
[C:1]([C:4]1([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[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[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[CH:13][CH:12]=2)[CH2:5][CH2:6][C:7](=[O:10])[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21514762HCID 21514762, compound2×

Product 1

HCID 215147374-(Hydroxymethyl)-4-(naphthalen-1-yl)cyclohexan-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 3.84 g. (0.0123 mole) of 4-carboxy-4-(1-naphthyl)cyclohexanone, ethylene ketal (prepared in Example 29) in 80 ml. of tetrahydrofuran is added to 0.5 g. (0.013 mole) of lithium aluminum hydride in 10 ml. of tetrahydrofuran. Following about 6 hours of heating at reflux the mixture is cooled in ice and treated successively with 0.5 ml. of water, 0.5 ml. of 15% sodium hydroxide solution and 1.5 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 3.95 g. (99% yield) of 4-hydroxymethyl-4-(1-naphthyl)cyclohexanone, ethylene ketal as an amorphous gum.

Workup

  1. temperatureof heating
  2. temperatureat reflux the mixture
  3. temperatureis cooled in ice
  4. additiontreated successively with 0.5 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 3.95 g

Sources & evidence

ORD record
ord-6e0acb77ffc34719b651bd5316a2c161
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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