Sodium Hydroxide → HCID 14347297, compound

HRID 2232844Notes

Reaction equation

HRID 2232844 reaction equation
C[O:2][C:3](=[O:28])/[CH:4]=[CH:5]/[CH:6]=[C:7](/[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)\[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-].[Na+]>CO>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20](/[C:7](/[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:6]/[CH:5]=[CH:4]/[C:3]([OH:28])=[O:2])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86742590HCID 86742590, compound

Product 1

HCID 14347297HCID 14347297, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As described in Example 99, (E,E)-5-(4-methoxyphenyl)-2,4-heptadecadienoic acid methyl ester (11.9 g) was saponified in a refluxing mixture of methanol (30 mL) and 2N NaOH (30 mL). After 2.5 hours the crude acid was isolated in the usual way and was crystallized from hexane to give 7.86 g of (E,E)-5-(4-methoxyphenyl)-2,4-heptadecadienoic acid. A sample was recrystallized from the same solvent to afford the analytical specimen, mp 85°-88° C.

Workup

  1. customAfter 2.5 hours the crude acid was isolated in the usual way
  2. customwas crystallized from hexane

Sources & evidence

ORD record
ord-237fd908c0604d879498b4f4f5fe44a9
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

Loading…