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

HRID 1764398Notes

Reaction equation

HRID 1764398 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-698cc70c582b4367bc762d658949b9f6
Source dataset
uspto-grants-1978_09
Patent number
US04116669

Reaction notes

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