Acetic Acid → HCID 66891073, compound

HRID 253302Notes

Reaction equation

HRID 253302 reaction equation
[F:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH:12]=[O:13])[CH:3]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[F:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH2:12][OH:13])[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 574231098-Fluoro-2,3-dihydro-1,4-benzodioxin-6-carboxaldehyde

Product 1

HCID 66891073HCID 66891073, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-fluoro-2,3-dihydro-1,4-benzodioxine-6-carbaldehyde (0.87 g: 4.8 mmol) was dissolved in ethanol (20 ml) and sodium borohydride (0.45 g; 11.95 mmol) was added at 0° C. The reaction mixture was stirred at rt for 2 h and poured into ice-water. The pH was adjusted to 5 by adding glacial acetic acid in portions and the aqueous mixture was extracted with ethyl acetate (80 ml). The organic phase was washed with water (30 ml), brine (30 ml), dried over sodium sulfate and concentrated under vacuum to give (8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methanol (0.84 g; 95% yield) as a yellow oil. 1H NMR (400 MHz, CD3OD) δ 6.66 (dd, 1H), 6.64 (br. s, 1H), 4.44 (s, 2H), 4.26 (s, 4H)

Workup

  1. extractionthe aqueous mixture was extracted with ethyl acetate (80 ml)
  2. washThe organic phase was washed with water (30 ml), brine (30 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9bfda7ac9c7a436ca5f8bc9452f80996
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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