Hydrochloric Acid → HCID 20230506, compound

HRID 2290813Notes

Reaction equation

HRID 2290813 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23](=[O:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:32])[CH3:31])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>CCOCC.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:23]([OH:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([OH:32])[CH3:31])[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 13565961HCID 13565961, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20230506HCID 20230506, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.8 g of 1-(3,4-dibenzyloxyphenyl)-1,8-nonanedione and 10 ml of tetrahydrofuran was added to a solution of 0.1 g of lithium aluminum hydride in 50 ml of ether under ice-cooling followed by stirring for 2 hours at room temperature. Then, 50 ml of toluene was added to the reaction mixture and the mixture was acidified by the addition of diluted hydrochloric acid. The toluene layer was collected, washed with an aqueous 5% sodium hydrogencarbonate solution, washed with water, dried over anhydrous magnesium carbonate, and concentrated under reduced pressure to provide 0.8 g of 1-(3,4-dibenzyloxyphenyl)-1,8-nonanediol as an oil.

Workup

  1. temperaturecooling
  2. customThe toluene layer was collected
  3. washwashed with an aqueous 5% sodium hydrogencarbonate solution
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium carbonate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88f955c65eb64a9393b9d0840df4c78e
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

Loading…