Diethyl Ether → 2-(2-Fluorobenzyloxy)-butane-1,4-diol

HRID 614696Notes

Reaction equation

HRID 614696 reaction equation
CO[C:3]([CH2:5][CH:6]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[F:21])[CH2:7]CC(OC)=O)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-].CC[O:30]CC>>[F:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][O:13][CH:6]([CH2:5][CH2:3][OH:4])[CH2:7][OH:30]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 538170452-(2-Fluorobenzyloxy)-butane-1,4-dicarboxylic acid dimethyl ester

Product 1

HCID 213266282-(2-Fluorobenzyloxy)-butane-1,4-diolYield 35.5%

Procedure

27 g (0.1 mol) of 2-(2-fluorobenzyloxy)-butane-1,4-dicarboxylic acid dimethyl ester were added dropwise, at 10° C., to a dispersion of 4.5 g of lithium aluminium hydride in 100 ml of absolute ether. After completion of the addition, the mixture was heated for 1 hour under reflux, and was cooled and hydrolysed with 35 ml of ice-water. After decanting the ether phase, the residue was repeatedly digested with ethanol. The combined organic phases were freed from the solvent and the residue was taken up in chloroform and chromatographed on a short silica gel column. The eluate was freed from the solvent and the residue was distilled. 7.5 g (35.5% of theory) of 2-(2-fluorobenzyloxy)-butane-1,4-diol of boiling point 155° C./0.5 mm Hg were obtained.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture was heated for 1 hour
  3. temperatureunder reflux
  4. customAfter decanting the ether phase
  5. customchromatographed on a short silica gel column
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-537607b1a995451783851cbe9ab4b280
Source dataset
uspto-grants-1979_03
Patent number
US04146384

Reaction notes

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