Hydrochloric Acid → HCID 131722454, compound

HRID 1532756Notes

Reaction equation

HRID 1532756 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[C:16](=[CH:18][CH:19]=[C:20]([OH:36])[C:21]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33](O)=[O:34])[OH:17].[H-].[Al+3].[Li+].[H-].[H-].[H-].[H][H].Cl>O1CCCC1.O.C(O)C>[C:20]1([C:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34])=[C:15]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][OH:2])[C:16](=[CH:18][CH:19]=1)[OH:17])[OH:36]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydride2×HCID 131721353HCID 131721353, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131722454HCID 131722454, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

The desired nonionic gemini surfactant, hydroquinone bislauryl alcohol was prepared as follows. Hydroquinone bislauric acid methyl ester (5.25 g) was dissolved in dry tetrahydrofuran (THF) at 0° C. Lithium aluminum hydride (LAH) (1.07 g) was added to the solution slowly. A large amount of hydrogen was generated. The reaction temperature was then raised to 25° C. After the reaction was stirred for an hour at this temperature, the reaction was stopped by adding ethanol to deactivate the excess LAH. The solution was mixed with water and then acidified with concentrated HCl. The final product was extracted twice with ether. The crude hydroquinone bislauryl alcohol was dried under vacuum. The product is an oily liquid (4.2 g) whose NMR spectrum agrees with the structure of the expected gemini compound. The reaction can be summarized as follows.

Workup

  1. extractionThe final product was extracted twice with ether
  2. dry with materialThe crude hydroquinone bislauryl alcohol was dried under vacuum
  3. customThe reaction

Sources & evidence

ORD record
ord-6e0568d5d2444a0193dd0cda792e66e0
Source dataset
uspto-grants-2001_03
Patent number
US06204297B1

Reaction notes

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