Hydrochloric Acid → HCID 14520267, compound

HRID 1722031Notes

Reaction equation

HRID 1722031 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[C:9]([O:22][CH3:23])=[C:10]([C:15]([O:20][CH3:21])=[C:16]([F:19])[C:17]=1[CH3:18])[C:11](OC)=[O:12].[H-].Cl>C(OCC)C.O.C(OCC)(=O)C>[F:7][C:8]1[C:9]([O:22][CH3:23])=[C:10]([C:15]([O:20][CH3:21])=[C:16]([F:19])[C:17]=1[CH3:18])[CH2:11][OH:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 166653HydrideHCID 20030225HCID 20030225, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14520267HCID 14520267, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium aluminium hydride (0.124 g) was added in a single portion to a solution of methyl 3,5-difluoro-2,6-dimethoxy-4-methylbenzoate (0.754 g) in dry diethyl ether (15 cm3) and the mixture stirred for one hour at the ambient temperature. Ethyl acetate was then added to decompose any remaining hydride, after which water was added and the mixture acidified with dilute hydrochloric acid. After extracting the mixture with diethyl ether, the extracts were dried over anhydrous magnesium sulphate and then concentrated by removal of the solvent by evaporation under reduced pressure to yield 3,5-difluoro-2,6-dimethoxy-4-methylbenzyl alcohol (0.66 g) which solidified on standing (mp. 80°-81° C.).

Workup

  1. extractionAfter extracting the mixture with diethyl ether
  2. dry with materialthe extracts were dried over anhydrous magnesium sulphate
  3. concentrationconcentrated by removal of the solvent by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d9d744c3063444d6a4b4bce4cc8f5804
Source dataset
uspto-grants-1989_08
Patent number
US04853414

Reaction notes

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