Tetrahydrofuran → 4-(3,4-Dimethoxyphenyl)-4-(hydroxymethyl)cyclohexan-1-one

HRID 1576214Notes

Reaction equation

HRID 1576214 reaction equation
[C:1]([C:4]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[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:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[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 204533371-(3,4-Dimethoxyphenyl)-4-oxocyclohexanecarboxylic Acid2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 215146714-(3,4-Dimethoxyphenyl)-4-(hydroxymethyl)cyclohexan-1-oneYield 62.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 19 g. (0.059 mole) of 4-carboxy-4-(3,4-dimethoxyphenyl)cyclohexanone, ethylene ketal (prepared in Example 28) in 290 ml. of tetrahydrofuran is added to 5.35 g. (0.141 mole) lithium aluminum hydride in 80 ml. of tetrahydrofuran. Following about 6 hours of heating at reflux the mixture is cooled in ice and treated successively with 5.4 ml. of water, 5.4 ml. of 15% sodium hydroxide solution and 16.2 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 11.4 g. (62.7% yield) of 4-hydroxymethyl-4-(3,4-dimethoxyphenyl)-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 5.4 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 11.4 g

Sources & evidence

ORD record
ord-aa3ba853a51e4bb7be5439817fbe3128
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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