Benzyl Chloride → 3-(2-Benzyloxy-5-methylphenyl)-3-phenylpropanol

HRID 900520Notes

Reaction equation

HRID 900520 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[CH:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:12][CH2:13][OH:14].[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1CCCCC1.CC(C)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:21]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[CH:11]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:12][CH2:13][OH:14])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 114819052-(3-Hydroxy-1-phenylpropyl)-4-methylphenol2×HCID 21916603Acetone cyclohexane

Product 1

HCID 112905073-(2-Benzyloxy-5-methylphenyl)-3-phenylpropanolYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

80 ml of an aqueous solution of NaOH (30% wt./vol.) and 10.6 g (0.033 moles) of tetrabutylammonium bromide (TBABr) were added to a suspension of 3-(2-hydroxy-5-methylphenyl)-3-phenylpropanol of the formula (VIII) (80 g, 0.330 moles) in toluene (320 ml). The internal temperature was adjusted to 50° C., 45.5 ml (0.396 moles) of benzyl chloride were added dropwise in approx. 1 h and the course of the reaction was monitored by means of TLC (eluent: cyclohexane/acetone: 70/30) until the substrate had completely disappeared. After 7 h, the reaction mixture was cooled to ambient temperature and the aqueous phase was removed. The organic phase was washed with water (3×100 ml), was then evaporated under a vacuum to remove the solvent and to obtain 104 g of 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol (IV) as a yellow-brown oil (yield 96%).

Workup

  1. customwas adjusted to 50° C.
  2. customthe aqueous phase was removed
  3. washThe organic phase was washed with water (3×100 ml)
  4. customwas then evaporated under a vacuum
  5. customto remove the solvent

Sources & evidence

ORD record
ord-c3a2ea12894a4fc18c27eba0dc1ff530
Source dataset
uspto-grants-2008_04
Patent number
US07358399B2

Reaction notes

Loading…