Sodium Hydroxide → HCID 15023592, compound

HRID 468696Notes

Reaction equation

HRID 468696 reaction equation
[OH-].[Na+].F[CH:4](F)[O:5][C:6]1[CH:7]=[C:8](/[C:16](/[CH3:23])=[CH:17]/[C:18]([O:20]CC)=[O:19])[CH:9]=[CH:10][C:11]=1[O:12][CH:13](F)F>CCO>[CH3:4][O:5][C:6]1[CH:7]=[C:8](/[C:16](/[CH3:23])=[CH:17]/[C:18]([OH:20])=[O:19])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86650356HCID 86650356, compound

Product 1

HCID 15023592HCID 15023592, compoundYield 114.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous 1.0 M NaOH (20 mL) was added to a solution of (E)-ethyl 3-(3,4-bis(difluoromethoxy)phenyl)-2-butenoate (0.36 g, 1.1 mmol) in EtOH (20 mL). The solution was stirred at rt for 16 h and then concentrated under reduced pressure to remove the EtOH. The aqueous phase was acidified with 1 M HCl and extracted with EtOAc, washed with water, brine, dried and concentrated. The crude product was recrystallised from EtOH/water to afford (E)-3-(3,4-dimethoxyphenyl)-2-butenoic acid (0.28 g, 85%) as a colourless crystalline solid; mp 73-74° C.; δH (500 MHz, CDCl3) 2.60 (d, J=1.5 Hz, 3H, CH3), 6.15 (q, J=1.5 Hz, 1H, C═CH), 6.55 (t, J=73 Hz, 2H, OCHF2), 7.28 (d, J5,6=8.0 Hz, 1H, H5), 7.36-7.38 (m, 2H, H2, H6); δC (125 MHz, CDCl3) 18.2, 115.6 (t, J=262 Hz), 115.7 (t, J=262 Hz), 117.2, 120.9, 122.1, 124.7, 140.6, 142.1, 143.1, 155.7, 170.1; νmax 1042, 1254, 1621, 1692, 2926 cm−1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove the EtOH
  3. extractionextracted with EtOAc
  4. washwashed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was recrystallised from EtOH/water

Sources & evidence

ORD record
ord-21c78a485d504f47ba8c74c2220ef374
Source dataset
uspto-grants-2014_01
Patent number
US08624056B2

Reaction notes

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