Sulfuric Acid → HCID 9815740, compound

HRID 1683466Notes

Reaction equation

HRID 1683466 reaction equation
[OH:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:8])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH3:16][C:17](=[CH2:19])[CH3:18].[OH-].[Na+]>ClCCl.O>[C:17]([O:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][Cl:8])=[CH:5][CH:4]=1)([CH3:19])([CH3:18])[CH3:16]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 14798Sodium HydroxideHCID 5107660[4-(Chloromethyl)phenyl]methanol

Product 1

HCID 9815740HCID 9815740, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A 5-gallon stirred pressure reactor was charged with p-hydroxymethylbenzyl chloride (600 g, 3.83 moles) in dichloromethane (6 liters). Concentrated sulfuric acid (60 mL) was charged to the reactor. Isobutylene gas was charged to the stirred solution for 2 hours at 10 psi. The temperature of the reaction was maintained at 20°-25° C. At the end of 24 hours the reaction was about 85% complete. The reaction mixture was diluted with water and the mixture adjusted to pH 7 by addition of 25% aqueous sodium hydroxide. The dichloromethane extract was dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was fractionally distilled on a 24 cm Vigreux column to provide 312 g (45% yield) of the desired product. The boiling point of the product was 115°-125° C. (2-3 mm Hg). 1H NMR spectral data were as follows: (CDCl3, 300 MHz): δ7.4 (s, 4H), 4.58 (s, 2H), 4.45 (s, 2H), 1.3 (s, 9H).

Workup

  1. temperatureThe temperature of the reaction was maintained at 20°-25° C
  2. customAt the end of 24 hours
  3. extractionThe dichloromethane extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. distillationThe residue was fractionally distilled on a 24 cm Vigreux column

Sources & evidence

ORD record
ord-365c0a944210478d8d56e0e66aa5e180
Source dataset
uspto-grants-1997_06
Patent number
US05637780

Reaction notes

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