Hydrochloric Acid → HCID 12527387, compound

HRID 1769801Notes

Reaction equation

HRID 1769801 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH2:6][CH:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+].S([O:26][CH3:27])(OC)(=O)=O.Cl>O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:26][CH3:27])=[C:4]([CH:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6][C:7]([OH:12])=[O:8])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 4291280HCID 4291280, compound

Product 1

HCID 12527387HCID 12527387, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

6-Chloro-4-phenyl-3,4-dihydrocoumarin (435 g, 1.68 mol. Preparation: T. Manimaran & V. T. Ramakrishnan, Ind. J. Chem. B 18 (1979) 328) is added to a hot solution of sodium hydroxide (140 g, 3.5 mol) in water (500 ml). The solution is chilled to 25° C. and dimethyl sulphate (442 g, 3.5 mol) is added dropwise during 1 h with stirring and cooling at 25°-35° C. The mixture is stirred for an additional 2 h whereupon a solution of 100 g of sodium hydroxide in 500 ml of water is added and the mixture is stirred until a clear solution is obtained. An excess of concentrated hydrochloric acid is added to precipitate the methoxy acid, which separates as an oil which slowly crystallizes. It is filtered off, washed with water and dried. Crystallization from 2-propanol gives colourless crystals of 3-(5-chloro-2-methoxyphenyl)-3-phenyl propionic acid, m.p. 144° C. Yield 455 g.

Workup

  1. temperaturecooling at 25°-35° C
  2. additionis added
  3. stirringthe mixture is stirred until a clear solution
  4. customis obtained
  5. customto precipitate the methoxy acid, which
  6. customslowly crystallizes
  7. filtrationIt is filtered off
  8. washwashed with water
  9. customdried
  10. customCrystallization from 2-propanol

Sources & evidence

ORD record
ord-d5f27f0fd3e24022a16f6ebce4998c13
Source dataset
uspto-grants-1995_01
Patent number
US05382600

Reaction notes

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