Water → HCID 86674044, compound

HRID 1773853Notes

Reaction equation

HRID 1773853 reaction equation
[C:1]([CH2:4][C:5]1([CH2:20][C:21]([OH:23])=[O:22])[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH3:19])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)([OH:3])=[O:2].O.[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]O>C1(C)C=CC=CC=1>[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][O:22][C:21]([CH2:20][C:5]1([CH2:4][C:1]([O:3][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][Br:25])=[O:2])[CH2:10][CH2:9][CH:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH3:19])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 779706-Bromo-1-hexanolHCID 67295308HCID 67295308, compound

Product 1

HCID 86674044HCID 86674044, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.0 g (30.8 mmol) of (4-carboxymethyl-4′-propylbicyclohexyl-4-yl)acetic acid are heated on a water separator for 6 h together with 15.0 g (80.4 mmol) of 6-bromo-1-hexanol and 0.50 g (2.90 mmol) of paratoluenesulfonic acid monohydrate in 150 ml of toluene. After cooling, the reaction mixture is subjected to absorptive filtration (SiO2, toluene), and the filtrate is concentrated to dryness. The crude product obtained in this way is used directly for the next reaction.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture is subjected to absorptive filtration (SiO2, toluene)
  3. concentrationthe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-940073f90a744930b7e7cf45ec3a3003
Source dataset
uspto-grants-2016_02
Patent number
US09255223B2

Reaction notes

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