2-Hydroxy-1-naphthaldehyde → 2-(2-Fluoroethoxy)-1-hydroxymethylnaphthalene

HRID 1087901Notes

Reaction equation

HRID 1087901 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH:15]=[O:16].OC1C=CC2C(=CC=CC=2)C=1C=O.[BH4-].[Na+]>C(O)C.O>[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[CH2:15][OH:16]

Participants

6

Reactant 3

HCID 128192-Hydroxy-1-naphthaldehydeHCID 4311764Sodium borohydrideHCID 150587342-(2-Fluoroethoxy)-1-naphthaldehyde

Product 1

HCID 150587332-(2-Fluoroethoxy)-1-hydroxymethylnaphthaleneYield 45.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 2.5 grams (0.012 mole) of 2-(2-fluoroethoxy)-1-naphthaldehyde (prepared by the method of Example 1 from 2-hydroxy-1-naphthaldehyde) and 0.6 gram (0.015 mole) of sodium borohydride in 35 ml of ethanol was stirred at room temperature for 24 hours. The mixture was diluted with water and extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 1.2 gram of 2-(2-fluoroethoxy)-1-hydroxymethylnaphthalene as a solid.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8c2fb2ca43f34f948047a93f82ef72e7
Source dataset
uspto-grants-1990_10
Patent number
US04960884

Reaction notes

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