Water → 2-(3-hydroxypropyl)phenol

HRID 1722638Notes

Reaction equation

HRID 1722638 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[CH:10][CH2:9]C1=O.[OH2:19].[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[OH:7][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH2:10][CH2:9][OH:19]

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 19595604HCID 19595604, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 2667422-(3-hydroxypropyl)phenol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To 20 g of lithium aluminum hydride in 200 ml of THF at 0° C. is added dropwise 84 g of 1-benzoxepin-2-one in 200 ml of THF. After addition is complete the reaction mixture is allowed to come to room temperature and stirred 11/4 hours. The reaction mixture is then chilled to 0° C. and 20 ml water, 20 ml 15% of NaOH and 60 ml H2O are sequentially added. The mixture is then diluted with ethyl acetate, acidified and filtered through celite. The EtOAc layer is separated, dried (MgSO4) and concentrated to obtain 3-(-o-hydroxyphenyl)-1-propanol as a brown oil which is used directly in the next step.

Workup

  1. additionAfter addition
  2. customto come to room temperature
  3. filtrationfiltered through celite
  4. customThe EtOAc layer is separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5ce6b396789c4575ae1aa102a5b43b72
Source dataset
uspto-grants-1989_08
Patent number
US04857517

Reaction notes

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