Phosphoric Acid → HCID 13050820, compound

HRID 1980616Notes

Reaction equation

HRID 1980616 reaction equation
[K].P(=O)(O)(O)[OH:3].[CH3:7][C:8]1[O:12][C:11]([CH:13]([CH:15]([CH3:18])[CH:16]=[CH2:17])O)=[CH:10][CH:9]=1.[Cl-].[Na+]>O>[CH3:18][CH:15]([C:13]1[C:11](=[O:12])[CH2:10][CH:9]([OH:3])[C:8]=1[CH3:7])[CH:16]=[CH2:17]

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 5234Sodium ChlorideHCID 5462222PotassiumHCID 20402319HCID 20402319, compound

Product 1

HCID 13050820HCID 13050820, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A buffer solution was prepared by dissolving potassium secondary phosphate (4 g) in water (800 ml) and adjusting the pH value to 7.5 (25° C.) with phosphoric acid. In a reaction vessel, 5-methyl-2-furyl-(α-methylallyl)-carbinol (20 g) and the entire amount of the buffer solution as prepared above were charged, and the temperature was elevated up to 180° C. in 55 minutes while stirring. The mixture was stirred at the same temperature for 5 hours, the inner pressure at this time being 9 kg/cm2. After ice-cooling, sodium chloride (100 g) was added thereto, and the mixture was extracted with methyl isobutyl ketone (200 ml) four times. The extract was concentrated at 60° C. under reduced pressure to remove methyl isobutyl ketone, and the resultant residue was subjected to distillation (112°-117° C./0.3 mmHg) to obtain 2-(α-methylallyl)-3-methyl-4-hydroxy-2-cyclopentenone (15.3 g). Yield, 76.5%. NMR spectrum (CDCl3 internal standard; TMS, δppm, 60 MHz): 5.99 (complex m, 1H, ##STR8## 5.08 (m, 1H, ##STR9## 4.84 (m, 1H, ##STR10## 4.63 (broad d, 1H, 4-H); 3.33 (m, 2H, 4-OH and ##STR11## 2.73 (dd, 1H, 5-H); 2.21 (dd, 1H, 5-H); 2.08 (s, 3H, 3-CH3); 1.21 (d, 3H, ##STR12##

Workup

  1. customA buffer solution was prepared
  2. customto 7.5 (25° C.)
  3. additionabove were charged
  4. stirringThe mixture was stirred at the same temperature for 5 hours
  5. temperatureAfter ice-cooling
  6. extractionthe mixture was extracted with methyl isobutyl ketone (200 ml) four times
  7. concentrationThe extract was concentrated at 60° C. under reduced pressure
  8. customto remove methyl isobutyl ketone
  9. distillationthe resultant residue was subjected to distillation (112°-117° C./0.3 mmHg)

Sources & evidence

ORD record
ord-6707e03d81664961973b206a6a0d5a77
Source dataset
uspto-grants-1985_04
Patent number
US04510329

Reaction notes

Loading…