Water → 2-Pentyl-1,3-propanediol

HRID 2292397Notes

Reaction equation

HRID 2292397 reaction equation
C([O:3][C:4]([CH:6]([C:14](OCC)=[O:15])[CH:7]([CH2:9][CH2:10][CH2:11][CH2:12]C)C)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S(=O)(=O)(O)O>[Na].C(OCC)C>[CH2:7]([CH:6]([CH2:14][OH:15])[CH2:4][OH:3])[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydride2×HCID 54122132HCID 54122132, compound

Product 1

HCID 1175092-Pentyl-1,3-propanediol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 5360545SodiumSolvent

Procedure

A solution of compound from Example 1 (59.2 g, 257 mmol) in sodium-dried diethyl ether (50 cm3) was added dropwise to a mixture of lithium aluminum hydride (19.5 g, 514 mmol) in dry diehtyl ether (450 cm3) with vigorous stirring and heated under gentle reflux. During this period, four 50 cm3 portions of dry diethyl ether were added. After further heating (1 h), water (75 cm3) was carefully added to decompose excess lithium aluminum hydride, followed by sulphuric acid (20%, 350 cm3). The aqueous layer was extracted with diethyl ether (2×100 cm3), the combined ethereal layers washed with water (2×100 cm3) and dried (MgSO4). The solvent was removed in vacuo to give the product as a colourless oil.

Workup

  1. temperatureheated under gentle reflux
  2. waitDuring this period
  3. additionwas carefully added
  4. extractionThe aqueous layer was extracted with diethyl ether (2×100 cm3)
  5. washthe combined ethereal layers washed with water (2×100 cm3)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-caad8c840b1442f4acdd25a99c1e66af
Source dataset
uspto-grants-1997_11
Patent number
US05683623

Reaction notes

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