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

HRID 2198597Notes

Reaction equation

HRID 2198597 reaction equation
[C:1]1([CH:7]([CH3:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.S(=O)(=O)(O)O.[C:16]1([OH:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(C)=O>[C:7]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[OH:22])([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 1118Sulfuric AcidHCID 7406Cumene

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stock solution containing 6 wt% DCP, 15 wt% cumene, 1 wt% water 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 IV 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 IV that best yields of AMS are obtained at temperatures over 100° C., e.g., 120° to 150° 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-e4d730badbaa460bb63bf9c1e369e9f4
Source dataset
uspto-grants-1982_11
Patent number
US04358618

Reaction notes

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