Water → Benzenepropanol,3-phenoxy-

HRID 1383235Notes

Reaction equation

HRID 1383235 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22](OCC)=[O:23])[CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C(OCC)C>[O:7]([C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH2:22][OH:23])[CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 54170266HCID 54170266, compound

Product 1

HCID 11775947Benzenepropanol,3-phenoxy-Yield 97.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred mixture of 7.4 grams (0.196 mole) of lithium aluminum hydride in 300 mL of dry diethyl ether under a nitrogen atmosphere was added 26.2 grams (0.098 mole) of ethyl 3-(3-phenoxyphenyl)acrylate in 300 mL of dry diethyl ether. The addition required 90 minutes to complete, and the reaction mixture was stirred overnight at ambient temperature. It was then cooled in an ice/water bath, and sequentially 14 mL of water, 14 mL of a 15% aqueous solution of sodium hydroxide, and 42 mL of water were all added dropwise. This mixture was filtered, and the filtrate was dried over anhydrous sodium sulfate. After being filtered, the solvent was evaporated under reduced pressure, leaving 21.9 grams of 3-(3-phenoxyphenyl)propanol as an oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionThe addition required 90 minutes
  2. temperatureIt was then cooled in an ice/water bath
  3. additionall added dropwise
  4. filtrationThis mixture was filtered
  5. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  6. filtrationAfter being filtered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1b7136ff4152479e9d0d9f37bc149cbc
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Reaction notes

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