Water → Methyl 3-{4-[(6-hydroxyhexyl)oxy]phenyl}prop-2-enoate

HRID 1810713Notes

Reaction equation

HRID 1810713 reaction equation
[CH3:1][O:2][C:3](/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)=[O:4].Cl[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C([O-])([O-])=O.[K+].[K+].O>CN1CCCC1=O>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 748286-Chloro-1-hexanolHCID 5319562Methyl-P-Coumarate

Product 1

HCID 67322893Methyl 3-{4-[(6-hydroxyhexyl)oxy]phenyl}prop-2-enoateYield 72%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 4-hydroxy cinnamate (40 g, 225 mmol) was dissolved in 1-methyl-2-pyrrolidinone (NMP, 300 mL). 6-Chlorohexanol (269 mmol, 36.8 g), anhydrous K2CO3 (37.2 g, 269 mmol) and catalytic amount of KI were added. The batch was stirred at 90° C. for 32 hours. Water was added to the cooled solution, which was subsequently extracted with ethyl acetate (EtOAc, 3×200 mL). The combined organics were washed with 10% KOH (2×100 mL), brine solution and then dried over MgSO4. The concentrated product was then recrystallized from a 1:1 mixture of EtOAc/hexanes to give 45 g (72% yield) of an off-white solid.

Workup

  1. extractionwas subsequently extracted with ethyl acetate (EtOAc, 3×200 mL)
  2. washThe combined organics were washed with 10% KOH (2×100 mL), brine solution
  3. dry with materialdried over MgSO4
  4. customThe concentrated product was then recrystallized from a 1:1 mixture of EtOAc/hexanes

Sources & evidence

ORD record
ord-b2fdbf81a30147d29629488e19defc10
Source dataset
uspto-grants-2013_01
Patent number
US08362151B2

Reaction notes

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