2-Methyl-3-buten-2-ol → HCID 20491272, compound

HRID 435206Notes

Reaction equation

HRID 435206 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[CH3:11][C:12](O)([CH:14]=[CH2:15])[CH3:13]>C(O)=O>[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([CH2:15][CH:14]=[C:12]([CH3:13])[CH3:11])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10]

Participants

4

Reactant 2

HCID 82572-Methyl-3-buten-2-olHCID 170162,3,6-Trimethylphenol

Product 1

HCID 20491272HCID 20491272, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
50 °C

Procedure

2,3,6-Trimethylphenol (68 g, 0.5 mol) and formic acid (100 mL) were combined and warmed to 50°-55° C. with vigorous agitation. To this mixture was added 2-methyl-3-buten-2-ol (47.3 g, 0.55 mol) dropwise over 0.25 h. The reaction mixture was stirred for an additional 2 h at 50° C., and then quenched into water (300 mL). The crude product was isolated by extraction with toluene (3×100 mL) followed by washing with water (200 mL), 5% sodium bicarbonate (2×100 mL), and brine (3×100 mL). Evaporation of the solvent and distillation afforded 61 g of the phenol, bp 145°-150° C. (2 mm). NMR (CDCl3) δ1.7 (6H, s), 2.2 (9H, s), 3.2 (2H, bd), 4.4 (1H, s, exchanged with D2O), 5.2 (1H, m), 6.8 (1H, s). IR (film) 3700, 1460, 1200, 1090 cm-1. MS (m/e) 204 (M+), 189, 174, 190, 136.

Workup

  1. temperaturewarmed to 50°-55° C. with vigorous agitation
  2. customquenched into water (300 mL)
  3. customThe crude product was isolated by extraction with toluene (3×100 mL)
  4. washby washing with water (200 mL), 5% sodium bicarbonate (2×100 mL), and brine (3×100 mL)
  5. customEvaporation of the solvent and distillation

Sources & evidence

ORD record
ord-21eccf79e0964150a72df3f43aaa346c
Source dataset
uspto-grants-1983_08
Patent number
US04400545

Reaction notes

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