Sodium hydride → HCID 13188176, compound

HRID 851328Notes

Reaction equation

HRID 851328 reaction equation
[CH2:1]1[CH2:16][O:15][C:3]2([CH2:8][CH2:7][CH2:6][CH2:5][C:4]2([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[CH3:9])[O:2]1.[H-].[Na+]>C1C=CC=CC=1>[CH2:9]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][C:4]1([CH3:9])[CH2:5][CH2:6][CH2:7][CH2:8][C:3]21[O:2][CH2:1][CH2:16][O:15]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 13188175HCID 13188175, compound

Product 1

HCID 13188176HCID 13188176, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1,1-ethylenedioxy-2-(4'-hydroxybutyl)-2-methylcyclohexane (26 g, 0.136 mol.) in benzene (100 ml) is added to a suspension of sodium hydride (6.53 g, 0.272 mol; 13.05 g of a 50% mineral oil dispersion freshly washed with pentane and benzene) in benzene (500 ml) in a nitrogen atmosphere. After 30 minutes benzylbromide (35 g, 020 mol) in benzene (100 ml) is added and the mixture is heated at reflux for 20 hours. The reaction mixture is cooled to room temperature and diluted with water (100 ml) and ether (500 ml). The organic layers are separated and washed with satd. NaCl (2×400 ml) and dried (MgSO4). The solvents are removed under reduced pressure and the crude product is chromatographed on SilicAR CC-7 (575 g) in hexane. Elution with 5% ethyl acetate/hexane gives 2-(4'-benzyloxybutyl)-1,1-ethylenedioxy-2-methylcyclohexane as a slightly yellowish oil (32.45 g, 90%): nmr (CDCl3)δ0.98 (s, 3H, CH3), 3.5 (t, 2H, --O--CH2 --CH2), 3.98 (s, 4H, ketal) 4.44 (s, 2H, O--CH2 --Ph), 7.3 (s, 5H, aromatic).

Workup

  1. wash13.05 g of a 50% mineral oil dispersion freshly washed with pentane and benzene) in benzene (500 ml) in a nitrogen atmosphere
  2. additionAfter 30 minutes benzylbromide (35 g, 020 mol) in benzene (100 ml) is added
  3. temperaturethe mixture is heated
  4. temperatureat reflux for 20 hours
  5. additiondiluted with water (100 ml) and ether (500 ml)
  6. customThe organic layers are separated
  7. washwashed with satd
  8. dry with materialNaCl (2×400 ml) and dried (MgSO4)
  9. customThe solvents are removed under reduced pressure
  10. customthe crude product is chromatographed on SilicAR CC-7 (575 g) in hexane
  11. washElution with 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-8be550510dff43b7af57d985b86137c1
Source dataset
uspto-grants-1983_05
Patent number
US04384126

Reaction notes

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