Hydrochloric Acid → 5-Pentyloxy-1-pentanol

HRID 2248044

Reaction equation

HRID 2248044 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][OH:14].Cl>CN(C)C=O>[CH2:4]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][OH:15])[CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80571-BromopentaneHCID 81051,5-PentanediolHCID 24758Sodium hydride

Product 1

HCID 141235455-Pentyloxy-1-pentanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 4.2 g) and then 12 ml of 1-bromopentane were added to a solution of 10 g of 1,5-pentanediol in 150 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 30 min. 3% hydrochloric acid was added to the reaction solution. After extraction with ether, the organic layer was dried and cencentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2) to obtain 6 g of the intended product.

Workup

  1. extractionAfter extraction with ether
  2. customthe organic layer was dried
  3. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=8/2)

Sources & evidence

ORD record
ord-de2b376a7de041be9f0904cecaa6380d
Source dataset
uspto-grants-1991_08
Patent number
US05037827

Linked notes

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