Sodium Hydroxide → HCID 3700253, compound

HRID 2049889Notes

Reaction equation

HRID 2049889 reaction equation
[Na].[H-].COCCO[Al+]OCCOC.[F:14][C:15]1[CH:30]=[CH:29][C:18]([O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[C:22](O)=[O:23])=[CH:17][CH:16]=1.[OH-].[Na+]>C1C=CC=CC=1>[F:14][C:15]1[CH:30]=[CH:29][C:18]([O:19][C:20]2[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=2[CH2:22][OH:23])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 30083672-(4-Fluorophenoxy)benzoic acidHCID 86736934HCID 86736934, compound

Product 1

HCID 3700253HCID 3700253, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
0 °C

Procedure

36.1 ml of 70% sodium-bis-(2-methoxyethoxy) aluminum hydride in benzene are added dropwise over a one hour span to a stirring mixture of 15 g of 2-(4-fluorophenoxy)benzoic acid in 150 ml of benzene under nitrogen at ambient temperature. After total addition, the reaction mixture is stirred for an additional 30 minutes and then permitted to stand for 4 days. Thereafter, the reaction mixture is cooled to 0° C. before adding 100 mls of 10% sodium hydroxide while stirring. Following this addition, the layers separate and the aqueous layer is extracted twice with 100 ml portions of benzene. The combined benzene solutions are successively washed twice with 100 ml portions of water, washed once with 60 ml of saturated sodium chloride solution and dried, providing a clear yellow oil. The oil is distilled at 118.5°-121.5° C. and 0.07 mm pressure to provide the clear, colorless liquid, 2-(4-fluorophenoxy)benzyl alcohol.

Workup

  1. additionAfter total addition
  2. waitto stand for 4 days
  3. stirringwhile stirring
  4. additionthis addition
  5. customthe layers separate
  6. extractionthe aqueous layer is extracted twice with 100 ml portions of benzene
  7. washThe combined benzene solutions are successively washed twice with 100 ml portions of water
  8. washwashed once with 60 ml of saturated sodium chloride solution
  9. customdried
  10. customproviding a clear yellow oil
  11. distillationThe oil is distilled at 118.5°-121.5° C.

Sources & evidence

ORD record
ord-d28fbc978fc94e9ab2f6ccb7ca84b64b
Source dataset
uspto-grants-1980_04
Patent number
US04198417

Reaction notes

Loading…