3,4-dihydro-2H-1-benzopyran-2-carboxylic acid → 2-(Hydroxymethyl)chroman

HRID 660413Notes

Reaction equation

HRID 660413 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11](O)=[O:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 27236653,4-dihydro-2H-1-benzopyran-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27948162-(Hydroxymethyl)chroman

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Chroman-2-carboxylic acid (4.3 g, 24 mmol) in THF (70 mL) was combined with 1M LAH in THF (30 mL, 30 mmol) and stirred at room temperature for 2 h. The reaction mixture was quenched with water and then stirred for 2 hours. The THF solution was decanted from the solid, which was washed with fresh THF. The combined THF solution was dried (Na2SO4) and evaporated in vacuo to yield chroman-2-yl-methanol as an oil.

Workup

  1. customThe reaction mixture was quenched with water
  2. stirringstirred for 2 hours
  3. customThe THF solution was decanted from the solid, which
  4. washwas washed with fresh THF
  5. dry with materialThe combined THF solution was dried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-7911a0063b644521b2878117d32d2f72
Source dataset
uspto-grants-2011_12
Patent number
US08084490B2

Reaction notes

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