Hydrochloric Acid → HCID 68796557, compound

HRID 450899Notes

Reaction equation

HRID 450899 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([O:24][CH3:25])[C:20]=1[CH:21]([CH3:23])[CH3:22])[C:14]([O:16]C)=O.O.Cl>CCOCC>[CH3:25][O:24][C:19]1[CH:18]=[C:13]([C:14]([OH:16])([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:12]=[C:11]([O:10][CH3:9])[C:20]=1[CH:21]([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7498Benzyl BromideHCID 24798870344396-17-4

Product 1

HCID 68796557HCID 68796557, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To Mg (0.252 g, 10.4 mmol) in dry ether (5 mL) was added benzylbromide (1 mL, 8.41 mL) in dry ether (3 mL) dropwise under reflux. After the addition was complete, the reaction mixture was further refluxed for 1 h. Methyl 3,5-dimethoxy-4-i-propylbenzoate (1.00 g, 4.20 mmol) in ether (15 mL) was added. After the ester completely disappeared, the reaction mixture was cooled to room temperature. Water (10 mL) was added followed by addition of 2N HCl (10 mL) to dissolve precipitate. The organic layer was separated and the aqueous layer was extracted with ether (3×50 mL). The extract was dried over anhydrous Na2SO4. Evaporation of solvent followed by flash chromatography using ethyl acetate:hexane (1:9) afforded 2-(3,5-dimethoxy-4-i-propylphenyl)-1,3-diphenylpropan-2-ol (1.29 g, 79%) as a white solid. 1HNMR (CDCl3, ppm): δ 1.28 (d, J=7.2 Hz, 6H), 3.08 (d, J=13.3 Hz, 2H), 3.35 (d, J=13.3 Hz, 2H), 3.6 (m, 1H), 3.95 (s, 6H), 6.44 (s, 2H), 6.9-7.5 (m, 10H).

Workup

  1. temperatureunder reflux
  2. additionAfter the addition
  3. temperaturethe reaction mixture was further refluxed for 1 h
  4. dissolutionto dissolve precipitate
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ether (3×50 mL)
  7. dry with materialThe extract was dried over anhydrous Na2SO4
  8. customEvaporation of solvent

Sources & evidence

ORD record
ord-0ebee85070234c53a7609fcee2fae8be
Source dataset
uspto-grants-2013_07
Patent number
US08487009B2

Reaction notes

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