Sodium hydride → Benzyloxyphenyl 6-methyloctyl ether

HRID 986099Notes

Reaction equation

HRID 986099 reaction equation
[H-].[Na+].C1(C([C:11]2[C:16]([CH2:17][O:18][CH2:19][C:20]3[C:25]([C:26]4C(=CC=[C:31]([OH:33])[CH:32]=4)O)=CC=CC=3)=[CH:15][CH:14]=[CH:13][CH:12]=2)=CC(=CC=1)O)O.Br[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH:40]([CH3:43])[CH2:41][CH3:42]>CN(C)C=O>[CH3:43][CH:40]([CH2:41][CH3:42])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][O:33][C:31]1[CH:32]=[CH:26][CH:25]=[CH:20][C:19]=1[O:18][CH2:17][C:16]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 135481051-Bromo-6-methyloctaneHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 20159468Benzyloxyphenyl 6-methyloctyl ether

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 100-ml 4-neck flask was charged with 3.74 g of NaH (containing 50% of oil) and 50 ml of N,N-dimethylformamide, and a solution of 15.46 g of hydroquinone monobenzyl ether in 30 ml of N,N-dimethylformamide was added under a nitrogen current over a period of 20 minutes in an ice water bath. After 20 minutes, 16 g of optically active 1-bromo-6-methyloctane was added over a period of 45 minutes, and reaction was carried out at room temperature for 6 hours. The reaction mixture was extracted with ether. The ether layer was washed with water, 5% NaOH, water and a saturated aqueous solution of sodium chloride in sequence and dried, and the organic solvent was distilled under reduced pressure to obtain a crude product. The crude product was purified to obtain 24.37 g of an ether compound.

Workup

  1. customreaction
  2. waitwas carried out at room temperature for 6 hours
  3. extractionThe reaction mixture was extracted with ether
  4. washThe ether layer was washed with water, 5% NaOH, water
  5. dry with materiala saturated aqueous solution of sodium chloride in sequence and dried
  6. distillationthe organic solvent was distilled under reduced pressure
  7. customto obtain a crude product
  8. customThe crude product was purified
  9. customto obtain 24.37 g of an ether compound

Sources & evidence

ORD record
ord-7561455b8ad04bf7a51d574c79016740
Source dataset
uspto-grants-1987_12
Patent number
US04710585

Reaction notes

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