alpha-Chloro-o-xylene → HCID 12884120, compound

HRID 443677Notes

Reaction equation

HRID 443677 reaction equation
[CH3:1][C:2]1([CH2:9][OH:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[O:3]1.[H-].[Na+].[CH3:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Cl>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH2:9][O:10][CH2:13][C:14]2[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=2[CH3:16])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[O:3]1

Participants

5

Reactant 3

HCID 11093alpha-Chloro-o-xyleneHCID 24758Sodium hydrideHCID 12634236(2,5,5-Trimethyl-tetrahydro-furan-2-yl)-methanol

Product 1

HCID 12884120HCID 12884120, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,5,5-Trimethyl-2-hydroxymethyl tetrahydrofuran (1.6 g) was added slowly to a stirred suspension of sodium hydride (0.4 g of 80% dispersion in oil) in dry toluene (55 ml). After the addition the mixture was heated under reflux for 1 hour. 2-Methylbenzyl chloride (1.8 g) was added and the mixture heated under reflux overnight. The cooled mixture was washed with water (x2) and dried and the solvent was removed under reduced pressure. The product was purified by chromatography on silica using methylene dichloride as eluent. Yield 80%.

Workup

  1. additionAfter the addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 1 hour
  4. temperaturethe mixture heated
  5. temperatureunder reflux overnight
  6. washThe cooled mixture was washed with water (x2)
  7. customdried
  8. customthe solvent was removed under reduced pressure
  9. customThe product was purified by chromatography on silica

Sources & evidence

ORD record
ord-31a0d20491b14ed286272cdd3e4cf655
Source dataset
uspto-grants-1981_04
Patent number
USRE030574

Reaction notes

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