Hydroquinone → n-Pentyl 2-(4-hydroxyphenoxy)-propionate

HRID 1154498Notes

Reaction equation

HRID 1154498 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[OH-].[Ca+2].[OH-].Br[CH:13]([CH3:22])[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:15]>CS(C)=O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH:13]([CH3:22])[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 522862Pentyl 2-bromopropanoateHCID 6093208Calcium Hydroxide

Product 1

HCID 12919931n-Pentyl 2-(4-hydroxyphenoxy)-propionateYield 70.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

264 g (2.4 moles) of hydroquinone were dissolved in 800 ml of anhydrous dimethylsulfoxide, and 89 g (1.2 moles) of calcium hydroxide were added. The mixture was stirred for 30 minutes at room temperature, after which it was cooled to 10° C. 268 g (1.2 moles) of n-pentyl 2-bromopropionate were added dropwise in the course of 3 hours, while maintaining this temperature. Thereafter, the mixture was left to warm up to room temperature, and stirred for 20 hours at this temperature. Finally, the mixture was worked up as described in Example 1. 214 g (0.85 mole) of n-pentyl 2-(4-hydroxyphenoxy)-propionate were obtained. Yield: 70.8%; bp.=149°-150° C./0.2 mbar. ##STR6##

Workup

  1. temperatureafter which it was cooled to 10° C
  2. temperaturewhile maintaining this temperature
  3. waitThereafter, the mixture was left
  4. temperatureto warm up to room temperature
  5. stirringstirred for 20 hours at this temperature

Sources & evidence

ORD record
ord-8fafea20ae1047b2bd6a1a25a5c10e9a
Source dataset
uspto-grants-1984_12
Patent number
US04489207

Reaction notes

Loading…