Hydrochloric Acid → 4-[(E)-3-(6-Benzyloxy-5-tert-butyl-4'-methyl-3-biphenylyl)-3-oxopropenyl]benzoic Acid

HRID 2377202Notes

Reaction equation

HRID 2377202 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:22](=[O:24])[CH3:23])=[CH:11][C:10]=1[C:25]([CH3:28])([CH3:27])[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([C:32]1[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=1)([OH:31])=[O:30].[OH-].[K+].Cl>CO>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[CH:13][C:12]([C:22](=[O:24])/[CH:23]=[CH:36]/[C:35]2[CH:38]=[CH:39][C:32]([C:29]([OH:31])=[O:30])=[CH:33][CH:34]=2)=[CH:11][C:10]=1[C:25]([CH3:28])([CH3:27])[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 120884-Formylbenzoic acidHCID 14797Potassium HydroxideHCID 120848201-(6-Benzyloxy-5-tert-butyl-4'-methyl-3-biphenylyl)ethanone

Product 1

HCID 120848214-[(E)-3-(6-Benzyloxy-5-tert-butyl-4'-methyl-3-biphenylyl)-3-oxopropenyl]benzoic AcidYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

970 mg (2.6 mmol) of 1-(6-benzyloxy-5-tert-butyl-4′-methyl-3-biphenylyl)ethanone are dissolved in 40 mL of methanol. 350 mg (2.3 mmol) of 4-carboxybenzaldehyde are added, followed by 1.23 mL (10 mmol) of 47% KOH. The reaction medium is stirred for 36 hours and then acidified with concentrated hydrochloric acid. The medium is extracted with ethyl acetate, and the residue obtained is purified by chromatography on a column of silica. The solid obtained is recrystallized from an ethyl ether/heptane mixture. A yellow powder is obtained (m=500 mg; yield=38%; m.p.=208° C.).

Workup

  1. extractionThe medium is extracted with ethyl acetate
  2. customthe residue obtained
  3. customis purified by chromatography on a column of silica
  4. customThe solid obtained
  5. customis recrystallized from an ethyl ether/heptane mixture
  6. customA yellow powder is obtained (m=500 mg; yield=38%; m.p.=208° C.)

Sources & evidence

ORD record
ord-9bc1f5f371a34a09bf22e40d8193e9d4
Source dataset
uspto-grants-2008_12
Patent number
US07468457B2

Reaction notes

Loading…