Tetrahydrofuran → HCID 12251261, compound

HRID 2398813Notes

Reaction equation

HRID 2398813 reaction equation
[CH2:1]1[O:21][C:4]2([CH2:9][CH2:8][C:7]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)([C:10](OC)=[O:11])[CH2:6][CH2:5]2)[O:3][CH2:2]1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH2:2]1[O:3][C:4]2([CH2:9][CH2:8][C:7]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)([CH2:10][OH:11])[CH2:6][CH2:5]2)[O:21][CH2:1]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 12251260HCID 12251260, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12251261HCID 12251261, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 22.3 g. (0.77 M) of 4-benzyl-4-carbomethoxy-1-cyclohexaneone ethylene ketal [5] (prepared as in Example 4B) in 220 ml. of tetrahydrofuran is added to 3 g. of lithium aluminum hydride in 30 ml. of tetrahydrofuran. The mixture is stirred at reflux temperature for about 5.5 hours and then cooled in ice. There is added successively 3 ml. of water, 3 ml. of aqueous 15% sodium hydroxide solution and 9 ml. of water. The inorganic gel is collected on a filter and the filtrate evaporated to dryness. The residue is recrystallized from methylene chloride: Skellysolve B to give 18.8 g. (93% yield) of 4-benzyl-4-hydroxymethylcyclohexan-1-one ethylene ketal (1), having a melting point of 76° to 78° C.

Workup

  1. temperatureat reflux temperature for about 5.5 hours
  2. temperaturecooled in ice
  3. additionThere is added successively 3 ml
  4. customThe inorganic gel is collected on
  5. filtrationa filter
  6. customthe filtrate evaporated to dryness
  7. customThe residue is recrystallized from methylene chloride
  8. customSkellysolve B to give 18.8 g

Sources & evidence

ORD record
ord-df65e8e66b7548188a7e98b1bd0b2e78
Source dataset
uspto-grants-1977_05
Patent number
US04025558

Reaction notes

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