Hydrochloric Acid → Benzhydrol

HRID 2108292Notes

Reaction equation

HRID 2108292 reaction equation
C([N-]C(C)C)(C)C.[Li+].Cl.[CH2:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[CH2:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C.C1C[O:27]CC1>C1COCC1>[C:10]1([CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[OH:27])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724682Lithium diisopropylamideHCID 86615247HCID 86615247, compound

Product 1

HCID 7037BenzhydrolYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

16.1 ml (120 mmol) of a 2M solution of lithium diisopropylamide in cyclo-hexane/ethylbenzene/THF are added under nitrogen and at −70° C. to a solution of 24.0 g (110 mmol) of the aromatic compound 24 in 150 ml of THF. After 1.5 hours at the low temperature, 22.1 g (100 mmol) of the aldehyde 23, dissolved in 50 ml of THF, are added to the batch. After 3 hours at −70° C., the batch is warmed to room temperature, hydrolysed and acidified using hydrochloric acid. The aqueous phase is extracted with MTB ether, and the organic phase is washed with sat. sodium chloride solution, dried over sodium sulfate, evaporated and passed through silica gel (MTB ether/n-heptane 1:10), giving 40.2 g (83%) of the diphenyl-methanol 25.

Workup

  1. additionare added to the batch
  2. extractionThe aqueous phase is extracted with MTB ether
  3. washthe organic phase is washed with sat. sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-af90bdee04c6435ab7f16f67a8b833d8
Source dataset
uspto-grants-2009_04
Patent number
US07514127B2

Reaction notes

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