Water → p-(Benzyloxy)phenethyl alcohol

HRID 652542Notes

Reaction equation

HRID 652542 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](OC)=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][OH:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2756645Methyl 2-(4-benzyloxyphenyl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 3017260p-(Benzyloxy)phenethyl alcoholYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 14.0 g of methyl 4-benzyloxyphenylacetate (7) in THF was slowly added with stirring to a solution of 2.0 g LAH in 500 mL of THF. The mixture was heated at reflux 1 h, cooled with ice, then treated sequentially with 2 mL water, 2 mL 15% NaOH, and 4 mL of water. The mixture was filtered and the filtrate evaporated to yield 10 g of crystalline 1-benzyloxy-4-(2-hydroxyethyl)benzene (8), m.p. 84°-85° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux 1 h
  3. temperaturecooled with ice
  4. filtrationThe mixture was filtered
  5. customthe filtrate evaporated

Sources & evidence

ORD record
ord-d3262109a67541dc99bc6ba412d024aa
Source dataset
uspto-grants-1987_06
Patent number
US04672071

Reaction notes

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