1,5-Pentanediol → PhCH2OCH2CH(CH3)O(CH2)5OH

HRID 2182019Notes

Reaction equation

HRID 2182019 reaction equation
[OH-].[K+].[OH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].O1CCOCC1.[C:16]1([CH2:22][O:23][CH2:24][CH:25](OS(C2C=CC(C)=CC=2)(=O)=O)[CH3:26])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[C:16]1([CH2:22][O:23][CH2:24][CH:25]([O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9])[CH3:26])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 81051,5-PentanediolHCID 14797Potassium Hydroxide2×HCID 312751,4-Dioxane2×HCID 562182Toluene-4-sulfonic acid, 2-benzyloxy-1-methylethyl ester

Product 1

HCID 85802962PhCH2OCH2CH(CH3)O(CH2)5OHYield 37.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Into another flask, KOH (25.8 g), HO(CH2)5OH (47.9 g) and dioxane (200 ml) were charged and stirred at 90° C. until KOH was dissolved. Then, from a dropping funnel, PhCH2OCH2CH(CH3)OTs (71.2 g) and dioxane (75 ml) were added at 90° C. over a period of 20 minutes. After further stirring at 80° C. for 20 hours, water (350 ml) was added. Extraction with dichloromethane (100 ml) was carried out three times, and the extracted organic phase was washed with water (150 ml), then dried over anhydrous magnesium sulfate, filtered and further concentrated. The concentrated liquid was purified by silica gel column (eluent: hexane/ethyl acetate) to obtain PhCH2OCH2CH(CH3)O(CH2)5OH(20.8 g).

Workup

  1. dissolutionwas dissolved
  2. extractionExtraction with dichloromethane (100 ml)
  3. washthe extracted organic phase was washed with water (150 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationfurther concentrated
  7. customThe concentrated liquid was purified by silica gel column (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-06eee858ce4e43eb8fadd7a6a83214fa
Source dataset
uspto-grants-2005_05
Patent number
US06894187B2

Reaction notes

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