HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Hydrochloric Acid → (E)-2-(4-(methoxymethoxy)phenyl)-3-o-tolylpent-2-enoic acid

HRID 884069
Notes
Print preview

Reaction equation

HRID 884069 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](/[C:11](=[C:17](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])/[CH2:18][CH3:19])/[C:12]([O:14]CC)=[O:13])=[CH:7][CH:6]=1.[OH-].[Na+].Cl>CO>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8](/[C:11](=[C:17](\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])/[CH2:18][CH3:19])/[C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86630294(E)-ethyl 2-(4-(methoxymethoxy)phenyl)-3-o-tolylpent-2-enoate

Product 1

HCID 68730809(E)-2-(4-(methoxymethoxy)phenyl)-3-o-tolylpent-2-enoic acidYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2a (240 mg, 0.677 mmol) in MeOH (7 ml) was added 2N NaOH (3.4 ml) and the mixture was stirred at 80° C. for 18 h. After cooling, 2 N HCl (3.4 ml) was added drop wise under ice cooling, and the whole was extracted with AcOEt, the organic layer was washed with brine, dried over Na2SO4, then concentrated. The residual solid was triturated with hexanes to give 3a (79%). 3a: colorless powder; 1H-NMR (CDCl3) δ 1.05 (3H, t, J=7.5 Hz), 2.08 (3H, s), 2.68 (1H, m), 2.77 (1H, m), 3.41 (3H, s), 5.07 (2H, s), 6.75 (2H, d, J=8.7 Hz), 6.93 (2H, d, J=8.7 Hz), 7.01 (2H, m), 7.05-7.09 (3H, m).

Workup

  1. temperatureAfter cooling
  2. extractionthe whole was extracted with AcOEt
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residual solid was triturated with hexanes

Sources & evidence

ORD record
ord-27ad2c00410b458c961e79cecdbcfdbd
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08236987B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes