Acetic Acid → HCID 12799966, compound

HRID 2412614Notes

Reaction equation

HRID 2412614 reaction equation
Cl.[CH2:2]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:22]([OH:24])=[O:23])[CH:19]=2)[NH:14]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH-].[Na+].C(O)(=O)C>C(O)C.O>[CH2:2]([CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:22]([OH:24])=[O:23])[CH:19]=2)[NH:14]1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 24839540HCID 24839540, compound

Product 1

HCID 12799966HCID 12799966, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

(RS)-2-(n-undecyl)indoline-5-carboxylic acid hydrochloride (32.9 g) in ethanol (150 ml) containing sodium hydroxide (10 g) and water (38 ml) was stirred and refluxed for 1.5 hours. Glacial acetic acid (15 ml) was added to the hot solution and the mixture was cooled to 0° C. and then diluted with water (600 ml). The solid was collected and was recrystallized from methanol to give (RS)-2-(n-undecyl)indoline-5-carboxylic acid (25.7 g), in the form of a white solid, m.p. 99°-103° C.

Workup

  1. temperaturerefluxed for 1.5 hours
  2. customThe solid was collected
  3. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-426e8cfaffa240679e464752185eec85
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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