Phenol → 4-(3-methylpentan-3-yl)phenol

HRID 2051597Notes

Reaction equation

HRID 2051597 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9](O)([CH2:12][CH3:13])[CH2:10][CH3:11].P(=O)(O)(O)O>C1C=CC=CC=1>[CH3:8][C:9]([C:4]1[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=1)([CH2:12][CH3:13])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 996PhenolHCID 1004Phosphoric AcidHCID 64933-Methyl-3-pentanol

Product 1

HCID 2235434-(3-methylpentan-3-yl)phenolYield 91%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of phenol (396 g, 4.2 mol), 3-methyl-3-pentanol (230 g. 2.25 mol), 85% phosphoric acid (50 g, 0.43 mol) and benzene (1.5 liters) was refluxed and the azeotroped water was collected in a Dean Stark trap (53 ml). The reaction mixture was cooled and transferred to a separatory funnel. A small bottom layer was separated and the top (organic) layer was washed with 500 ml portions of water until the pH of the washes was 7 (neutral). The solvent was removed on a rotary evaporator. Distillation of the residual oil under vacuum gave the desired 4-(3-methylpent-3-yl)phenol: 365 g, 91% yield; bp 112° C. (1.0 mm); mol wt. 178 (ms); nmr, 0.68 (6H, t, J=8 2-methyls), 1.26 (3H, s, methyl), 1.4-2.0 (4H, m, --CH2 --), 6.28 (1H, s, hydroxyl), 6.8-7.3 (4H, m, aromatics); ir, 3260, 2980, 2940, 2890, 1615, 1600, 1515, 1466, 1380, 1250, 1190, 1120, 830 cm-1.

Workup

  1. temperaturewas refluxed
  2. customthe azeotroped water was collected in a Dean Stark trap (53 ml)
  3. temperatureThe reaction mixture was cooled
  4. customtransferred to a separatory funnel
  5. customA small bottom layer was separated
  6. washthe top (organic) layer was washed with 500 ml portions of water until the pH of the washes
  7. customThe solvent was removed on a rotary evaporator
  8. distillationDistillation of the residual oil under vacuum

Sources & evidence

ORD record
ord-e45009510cb449eebe6011058619fee9
Source dataset
uspto-grants-1980_01
Patent number
US04181631

Reaction notes

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