Allyl bromide → 1-(Allyloxy)-4-chloro-2-cyclohexylbenzene

HRID 2115910Notes

Reaction equation

HRID 2115910 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:3]=1.[H-].[Na+].[CH2:17](Br)[CH:18]=[CH2:19]>CN(C)C=O>[CH2:19]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 831204-Chloro-2-cyclohexylphenol

Product 1

HCID 689624291-(Allyloxy)-4-chloro-2-cyclohexylbenzeneYield 106.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-2-cyclohexylphenol (23.00 g, 0.109 mol) in N,N-dimethylformamide (600 mL) was added sodium hydride (4.56 g, 0.114 mol, 60 wt. %) followed by allyl bromide (14.51 g, 0.120 mol) and the reaction mixture was allowed to stir at room temperature for 5 h. The solvent was removed in vacuo and the residue diluted with water (500 mL) and extracted with ethyl acetate (2×300 mL). The combined organic layers were washed with water (500 mL), saturated aqueous sodium chloride (500 mL), dried (magnesium sulfate), and the solvent removed in vacuo to give 29.0 g of 1-(allyloxy)-4-chloro-2-cyclohexylbenzene as a brown oil. Treatment of the allyl ether in refluxing mesitylene generally according to the procedure described for Intermediate 8 provided 18.0 g of 2-allyl-4-chloro-6-cyclohexylphenol. Treatment of the phenol (6.5 g, 0.026 mol) with 3-chloroperoxybenzoic acid (9.88 g, 0.045 mol, 77%) followed by potassium carbonate (10.00 g, 0.072 mol) generally according to the procedure described for Intermediate 9 afforded 4.6 g (67%) of (±)-(5-chloro-7-cyclohexyl-2,3-dihydro-1-benzofuran-2-yl)methanol as a white solid. mp 67-69° C.; Anal. calcd. for C15H19ClO2: C, 67.54; H, 7.18. Found: C, 67.81; H, 6.98.

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue diluted with water (500 mL)
  3. extractionextracted with ethyl acetate (2×300 mL)
  4. washThe combined organic layers were washed with water (500 mL), saturated aqueous sodium chloride (500 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-1c4879f2be984c66af5e01ab6784e3cf
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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