Hydrochloric Acid → 3-(2-Benzyloxy-5-methylphenyl)-3-phenylpropanol

HRID 899562Notes

Reaction equation

HRID 899562 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]([C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[CH:14][C:13]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.COCCO[AlH2-]OCCOC.[Na+].[H-].COCCO[Al+]OCCOC.[Na+].[H-].Cl>C1(C)C=CC=CC=1.O>[CH2:20]([O:19][C:13]1[CH:14]=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[CH:5]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:4][CH2:3][OH:2])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11667650Methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionateHCID 16684438Red-AlHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 112905073-(2-Benzyloxy-5-methylphenyl)-3-phenylpropanolYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

810 g of methyl-3 -(2-benzyloxy-5-methylphenyl)-3 -phenylpropionate and 3240 ml of toluene were stirred at 25-30° C. for about 20 minutes. 842.5 ml of VITRIDE® (sodium bis(2-methoxyethoxy)aluminum hydride, 65% w/w in toluene) was added slowly to the reaction mass below 40° C. under a nitrogen atmosphere, and stirred for about 20-25 minutes. A solution of 1620 ml of concentrated hydrochloric acid and 1620 ml of water was added slowly to the reaction mass and stirred for 15-20 minutes. The aqueous layer was separated and extracted with toluene (810 ml). Combined organic layers were washed with 4050 ml of water and then with 10% aqueous sodium carbonate solution (4050 ml). Organic layer was further washed with water (2×2430 ml) and the solvent was distilled under vacuum (about 600 mm Hg) below 100° C. 3240 ml of hexane was added to the residue at 30-40° C. and stirred for 2-3 hours. It was further cooled to 20-25° C. and stirred for 2-3 hours. Filtered the solid and washed with hexane (810 ml). Dried the solid at 25-30° C. under vacuum (about 600 mm Hg) for 2-3 hours to get 680 g of the title compound.

Workup

  1. stirringstirred for 15-20 minutes
  2. customThe aqueous layer was separated
  3. extractionextracted with toluene (810 ml)
  4. washCombined organic layers were washed with 4050 ml of water
  5. washOrganic layer was further washed with water (2×2430 ml)
  6. distillationthe solvent was distilled under vacuum (about 600 mm Hg) below 100° C
  7. addition3240 ml of hexane was added to the residue at 30-40° C.
  8. stirringstirred for 2-3 hours
  9. stirringstirred for 2-3 hours
  10. filtrationFiltered the solid
  11. washwashed with hexane (810 ml)
  12. customDried the solid at 25-30° C. under vacuum (about 600 mm Hg) for 2-3 hours

Sources & evidence

ORD record
ord-77e28764096e41a6a56814d2f66249f4
Source dataset
uspto-grants-2008_04
Patent number
US07355077B2

Reaction notes

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