HCID 12789562, compound → Benzenemethanol, 2-[4-(hydroxymethyl)phenoxy]-

HRID 1732725Notes

Reaction equation

HRID 1732725 reaction equation
C([O:3][C:4]([C:6]1[CH:21]=[CH:20][C:9]([O:10][C:11]2[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=2[C:13](O)=[O:14])=[CH:8][CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:14][CH2:13][C:12]1[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=1[O:10][C:9]1[CH:20]=[CH:21][C:6]([CH2:4][OH:3])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 12789562HCID 12789562, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 53889568Benzenemethanol, 2-[4-(hydroxymethyl)phenoxy]-Yield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(4'-ethoxycarbonylphenoxy)benzoic acid (35 g) in dry tetrahydrofuran (120 ml) was added dropwise to a stirred suspension of lithium aluminum hydride (9.3 g) in dry tetrahydrofuran (300 ml) at room temperature. After the addition, the mixture was refluxed with stirring for 4 hours, and then the excess of lithium aluminum hydride was destroyed by cautious addition of water. The mixture was concentrated and dilute hydrochloric acid was added to the residue. The resulting mixture was extracted with chloroform and the extracts were washed with water. Concentration of the dried extracts gave crude 4-(2'-hydroxymethylphenoxy)benzyl alcohol (25 g) as an oil, IRνmaxfilm cm-1 : 3300 (OH).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed
  3. customthe excess of lithium aluminum hydride was destroyed by cautious addition of water
  4. concentrationThe mixture was concentrated
  5. additiondilute hydrochloric acid was added to the residue
  6. extractionThe resulting mixture was extracted with chloroform
  7. washthe extracts were washed with water

Sources & evidence

ORD record
ord-9dbb2cd23ff84dbc94aca82a4555a30d
Source dataset
uspto-grants-1980_12
Patent number
US04238620

Reaction notes

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