(R)-1,4-Benzodioxane-2-carboxylic acid → (S)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

HRID 453837Notes

Reaction equation

HRID 453837 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[C:11](O)=[O:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 687062(R)-1,4-Benzodioxane-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 676612(S)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-2,3-Dihydro-benzo[1,4]dioxine-2-carboxylic acid (27.9 mmol, 5.02 g) was dissolved in dry THF (30 ml). LiAlH4 (56.9 mmol, 2.16 g) was added. The mixture was refluxed for 70 minutes. After cooling, the reaction was quenched with water and 1 M NaOH. The mixture was filtrated through Celite and evaporated to dryness. This gave 4.3 g of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 70 minutes
  2. temperatureAfter cooling
  3. customthe reaction was quenched with water and 1 M NaOH
  4. filtrationThe mixture was filtrated through Celite
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5bbbff1dd90c422aaaf5649ebbf4db01
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Reaction notes

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