2,3-Dihydroxybenzaldehyde → HCID 22164153, compound

HRID 1087893Notes

Reaction equation

HRID 1087893 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([O:13][CH2:14][CH2:15][F:16])=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8].OC1C(O)=CC=CC=1C=O.[BH4-].[Na+]>C(O)C>[F:16][CH2:15][CH2:14][O:13][C:12]1[CH:11]=[CH:10][CH:9]=[C:6]([CH2:7][OH:8])[C:5]=1[O:4][CH2:3][CH2:2][F:1]

Participants

5

Reactant 3

HCID 905792,3-DihydroxybenzaldehydeHCID 4311764Sodium borohydrideHCID 15058684HCID 15058684, compound

Product 1

HCID 22164153HCID 22164153, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a dry nitrogen atmosphere a mixture of 6.0 grams (0.026 mole) of 2,3-di(2-fluoroethoxy)benzaldehyde (prepared by the method of Example 1 from 2,3-dihydroxybenzaldehyde) and 1.3 gram (0.034 mole) of sodium borohydride in 130 ml of ethanol was stirred at room temperature for approximately 18 hours. The reaction was quenched with dilute hydrochloric acid, and the mixture was extracted with diethyl ether. The extract was washed with dilute hydrochloric acid followed by an aqueous, saturated sodium chloride solution. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to yield 5.4 grams of 1,2-di-(2-fluoroethoxy)-3-hydroxymethylbenzene as a solid.

Workup

  1. customThe reaction was quenched with dilute hydrochloric acid
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe extract was washed with dilute hydrochloric acid
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0f77282acf3d44e48b67862c62af58d7
Source dataset
uspto-grants-1990_10
Patent number
US04960884

Reaction notes

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