2-Methyl-3-buten-2-ol → HCID 14710051, compound

HRID 2286134Notes

Reaction equation

HRID 2286134 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[CH3:10][C:11](O)([CH:13]=[CH2:14])[CH3:12]>P(=O)(O)(O)O>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:14][CH:13]=[C:11]([CH3:12])[CH3:10])[CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9]

Participants

4

Reactant 2

HCID 82572-Methyl-3-buten-2-olHCID 113352,6-Dimethylphenol

Product 1

HCID 14710051HCID 14710051, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

To a mixture of 2,6-dimethylphenol (122 g, 1 mol) and 85% phosphoric acid (60 mL) was added 2-methyl-3-buten-2-ol (103 g, 1.2 mol) with efficient stirring at 35°-43° C. during 1 h. After stirring for an additional 3.5 h at 25° C., the mixture was quenched into ice and extracted with hexane. The combined hexane extracts were washed successively with 1 N sodium hydroxide (100 mL), 5% sodium bicarbonate (300 mL) and brine (200 mL). The organic layer was dried, the solvent evaporated, and the residue fractionated to yield 92 g of 2,6-dimethyl-4-(3-methyl-2-butenyl)phenol bp 108°-111° C. (1 mm). NMR (CDCl3) δ1.7 (6H, s), 2.2 (6H, s), 3.2 (2H, bd), 4.4 (1H, s, exchanged with D2O), 5.3 (1H, m), 6.8 (2H, s). IR (film) 3500, 1225, 1150, 870 cm-1. MS (m/e) 190 (M+), 175, 160, 135, 91.

Workup

  1. stirringAfter stirring for an additional 3.5 h at 25° C.
  2. customthe mixture was quenched into ice
  3. extractionextracted with hexane
  4. washThe combined hexane extracts were washed successively with 1 N sodium hydroxide (100 mL), 5% sodium bicarbonate (300 mL) and brine (200 mL)
  5. customThe organic layer was dried
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-20da496ae94645ebb4256c8215c6c91f
Source dataset
uspto-grants-1982_04
Patent number
US04326997

Reaction notes

Loading…