Phenol → HCID 19386628, compound

HRID 1981386Notes

Reaction equation

HRID 1981386 reaction equation
[C:1]1(O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][CH:9]([OH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.S(=O)(=O)(O)O>C(C1C=CC=CC=1)C>[C:1]1([CH2:8][CH:9]([O:16][CH:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 1118Sulfuric AcidHCID 74091-Phenylethanol

Product 1

HCID 19386628HCID 19386628, compound

Reagents, catalysts & solvents 1

HCID 7500EthylbenzeneSolvent

Procedure

Phenol (21.21 grams; 0.25 mole) and methylbenzyl alcohol (30.5 grams; 0.25 mole) in 100.00 grams of ethylbenzene were refluxed at a temperature of from about 135° to 140° C. for about four hours with 0.500 grams (0.33 weight percent) concentrated sulfuric acid. Water was removed overhead as a azeotrope and was collected in a Dean-Stark trap. Methylbenzyl alcohol conversion was quantitative but only 8% selectivity to α-phenylmethylbenzyl ether was obtained. The remaining product was styrene (74.8% selectivity) and styrene polymer.

Workup

  1. customWater was removed overhead as a azeotrope
  2. customwas collected in a Dean-Stark trap

Sources & evidence

ORD record
ord-b4b2be29661e40fda26fbec0f2c02627
Source dataset
uspto-grants-1985_04
Patent number
US04514576

Reaction notes

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