Hydroquinone → Butyl 2-(4-hydroxyphenoxy)propanoate

HRID 1154499Notes

Reaction equation

HRID 1154499 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-].[Ca+2].[OH-].Cl[CH:13]([CH3:21])[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15]>CS(C)=O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH:13]([CH3:21])[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 123534Butyl 2-chloropropanoateHCID 6093208Calcium Hydroxide

Product 1

HCID 12919928Butyl 2-(4-hydroxyphenoxy)propanoateYield 46.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

121 g (1.1 moles) of hydroquinone were dissolved in 500 ml of dimethylsulfoxide, 37 g (0.5 mole) of calcium hydroxide were added to the solution, and the mixture was stirred for 1 hour at 45°-50° C. Thereafter, 82.3 g (0.455 mole) of optically active n-butyl 2-chloropropionate (αD20 =-13.0°) were added dropwise in the course of 1 hour at the same temperature. The mixture was stirred for a further 3 hours at 45°-50° C., cooled, and worked up as described in Example 1. 49.7 g (0.21 mole) of optically active n-butyl 2-(4-hydroxyphenoxy)-propionate were obtained. Yield: 46.2%; bp. =150°-152° C./0.22 mbar; αD20 =+11.8° ##STR7##

Workup

  1. stirringThe mixture was stirred for a further 3 hours at 45°-50° C.
  2. temperaturecooled

Sources & evidence

ORD record
ord-86ee785db5494347bc7344a5c6d7d3cc
Source dataset
uspto-grants-1984_12
Patent number
US04489207

Reaction notes

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