Hydrochloric Acid → HCID 21273115, compound

HRID 1382705Notes

Reaction equation

HRID 1382705 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[CH2:10][CH2:11][CH2:12][CH:13]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C(OCC)(=O)C.Cl>O1CCCC1.O>[CH2:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1/[CH:14]=[CH:13]/[CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 53928156HCID 53928156, compound

Product 1

HCID 21273115HCID 21273115, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.8 g of lithiumaluminium hydride are added in portions, over a period of approximately one hour, to a solution, stirred under a nitrogen atmosphere, of 34.4 g of 6-(2-nonylphenyl)-5-hexenoic acid methyl ester (cf. EP-OL 0 123 543) in 300 ml of absolute tetrahydrofuran. After a further 10 minutes 30 ml of ethyl acetate and then 30 ml of water are added dropwise. The reaction mixture is acidified by the addition of 1N hydrochloric acid and extracted repeatedly with ethyl acetate. After the combined organic phases have been dried and concentrated by evaporation, the crude product that remains is purified by chromatography on silica gel with dichloromethane to yield the title compound in the form of a yellowish oil.

Workup

  1. extractionextracted repeatedly with ethyl acetate
  2. customAfter the combined organic phases have been dried
  3. concentrationconcentrated by evaporation
  4. customthe crude product that remains is purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-0b5516d10bed405baf99532430493a1e
Source dataset
uspto-grants-1989_02
Patent number
US04808572

Reaction notes

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