Hydrochloric Acid → (2-phenylcyclopropyl)methanol

HRID 1602570Notes

Reaction equation

HRID 1602570 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C@@H:13]2[CH2:15][C@H:14]2[C:16](O)=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.Cl>O1CCCC1>[OH:17][CH2:16][C@@H:14]1[CH2:15][C@H:13]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 237413trans-2-Phenylcyclopropanecarboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 1561175(2-phenylcyclopropyl)methanolYield 103.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

152 mg of lithium aluminium hydride suspended in 10 ml of tetrahydrofuran was mixed with 324 mg of trans-2-phenylcyclopropane-1-carboxylic acid under cooling with ice and stirred at the same temperature for 30 minutes and then at room temperature for 2 hours. Water was gradually added to the reaction solution and then 1N hydrochloric acid was gradually added. The reaction solution was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1→2/1] to give 307 mg of trans-l-(hydroxymethyl)-2-phenylcyclopropane as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. waitat room temperature for 2 hours
  3. extractionThe reaction solution was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=3/1→2/1]

Sources & evidence

ORD record
ord-f096ecb36bc648428e9d36356d5ed396
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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