Aluminium lithium hydride → HCID 178444272, compound

HRID 1380780Notes

Reaction equation

HRID 1380780 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11]>O1CCCC1>[CH2:7]([C@H:12]1[CH2:13][CH2:14][C@H:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:16][CH2:17]1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178444271HCID 178444271, compound

Product 1

HCID 178444272HCID 178444272, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 930 mg of lithium aluminium hydride in 100 ml of absolute tetrahydrofuran was placed at 0° C. in a sulphonation flask and treated within 20 minutes with a solution of 8.2 g of 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxaldehyde in 100 ml of absolute tetrahydrofuran. After completion of the addition, the mixture was stirred for a further 2 hours while warming to room temperature, subsequently cautiously quenched with 100 ml of 1N sulphuric acid and extracted three times with 200 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. There were obtained 7.90 g (96%) of 4'-(trans-4-pentylcyclohexyl)-4-biphenylmethanol as a colourless, crystalline mass (purity 99.4% in accordance with gas chromatography) which was used in the following step without further purification. M.p. 180.4° C.; Rf value [petroleum ether/ethyl acetate (9:1)]: educt 0.70, product 0.30.

Workup

  1. customwas placed at 0° C. in a sulphonation flask
  2. additionAfter completion of the addition
  3. customsubsequently cautiously quenched with 100 ml of 1N sulphuric acid
  4. extractionextracted three times with 200 ml of methylene chloride each time
  5. washThe organic phases were washed twice with 100 ml of water each time
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0a444a6b48bd447caf4823eaf924fe0d
Source dataset
uspto-grants-1986_04
Patent number
US04583826

Reaction notes

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