Hydrochloric Acid → 4-(4-Fluorophenyl)-4-(hydroxymethyl)cyclohexan-1-one

HRID 1576212Notes

Reaction equation

HRID 1576212 reaction equation
[C:1]([C:4]1([C:11]2[CH:16]=[CH:15][C:14]([F: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-].Cl>O>[OH:2][CH2:1][C:4]1([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[CH2:5][CH2:6][C:7](=[O:10])[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 219553321-(4-Fluorophenyl)-4-oxocyclohexanecarboxylic acid2×

Product 1

HCID 215147454-(4-Fluorophenyl)-4-(hydroxymethyl)cyclohexan-1-oneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 18.2 g. (0.065 mole) of 4-carboxy-4-(4-fluorophenyl)cyclohexanone, ethylene ketal (prepared in Example 26) in 200 ml. of tetrahydrofuran is added to 5.9 g. (0.155 mole) of lithium aluminum hydride in 50 ml. of tetrahydrofuran. Following about 6 hours of heating at reflux, the mixture is cooled in ice and treated with 10 ml. of water and 200 ml. of 2.5 N hydrochloric acid. The organic layer is washed with water and brine and then evaporated to dryness to give 18.18 g. (99% yield) of 4-hydroxymethyl-4-(4-fluorophenyl)cyclohexanone, ethylene ketal as an amorphour gum.

Workup

  1. temperatureof heating
  2. temperatureat reflux
  3. temperaturethe mixture is cooled in ice
  4. additiontreated with 10 ml
  5. washThe organic layer is washed with water and brine
  6. customevaporated to dryness
  7. customto give 18.18 g

Sources & evidence

ORD record
ord-35b6ce0a17a64bf2b7ddf40f4d5f4b73
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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