Phenol → Phenol, o-(alpha,alpha-dimethylbenzyl)-

HRID 2198596Notes

Reaction equation

HRID 2198596 reaction equation
COC(OC(OC)=O)=O.[C:10]1([CH:16]([CH3:18])[CH3:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S(=O)(=O)(O)O.[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[C:16]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[OH:30])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 996PhenolHCID 1118Sulfuric AcidHCID 3086Dimethyl dicarbonateHCID 7406Cumene

Product 1

HCID 123377Phenol, o-(alpha,alpha-dimethylbenzyl)-

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stock solution containing 6 wt% DMPC, 15 wt% cumene and 50 ppm sulfuric acid with the balance composed of equimolar phenol and acetone was distributed among several melting point capillary tubes which were subsequently sealed and heated for various lengths of time in a stirred oil bath. The tubes were then quickly cooled by immersion in an ice bath and the contents were analyzed by gas chromatography. The amount of AMS formed increased with time up to a maximum yield and then declined as increased amounts of AMS dimers and cumylphenol were formed. Table II records the maximum AMS yield obtained at each temperature, as well as the heating time required to reach that yield. It is clear from the data of Table II that the best yields of AMS were obtained at temperatures over 90° C., e.g., 120° and 130° C.

Workup

  1. customwere subsequently sealed
  2. temperatureheated for various lengths of time in a stirred oil bath
  3. temperatureThe tubes were then quickly cooled by immersion in an ice bath
  4. customThe amount of AMS formed
  5. temperatureincreased with time up to
  6. customa maximum yield
  7. temperatureas increased amounts of AMS dimers

Sources & evidence

ORD record
ord-f347a73640a64eb6a1f29ce0bb010cb7
Source dataset
uspto-grants-1982_11
Patent number
US04358618

Reaction notes

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