Acetic Acid → 1-(3-Phenoxyphenyl)propan-1-ol

HRID 1907017Notes

Reaction equation

HRID 1907017 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](O)(=O)[CH3:17]>O1CCCC1.C(OCC)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]([OH:12])[CH2:16][CH3:17])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 382843-Phenoxybenzaldehyde

Product 1

HCID 151854771-(3-Phenoxyphenyl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 25.1 g of 3-phenoxybenzaldehyde in 23 ml of an anhydrous tetrahydrofuran is added dropwise to 60 ml of 3-N-ethylmagnesium bromide in ethyl ether, cooled in an ice bath under a nitrogen atmosphere, over a period of about 11/2 hours. The reaction mixture is stirred overnight and warmed to room temperature, after which time it is poured over ice containing 12 ml of acetic acid. The organic and aqueous phases are separated and the aqueous phases extracted twice with ethyl ether. The ethereal extracts are combined and washed with a solution prepared from 3 g of sodium carbonate and 40 ml of water. The aqueous wash layers are extracted further with ethyl ether and the combined ethereal extracts are dried over anhydrous sodium sulfate and filtered. The ether is removed under reduced pressure to yield 29.45 g of 1-(3-phenoxyphenyl)propan-1-ol.

Workup

  1. temperaturecooled in an ice bath under a nitrogen atmosphere, over a period of about 11/2 hours
  2. customThe organic and aqueous phases are separated
  3. extractionthe aqueous phases extracted twice with ethyl ether
  4. washwashed with a solution
  5. customprepared from 3 g of sodium carbonate and 40 ml of water
  6. extractionThe aqueous wash layers are extracted further with ethyl ether
  7. dry with materialthe combined ethereal extracts are dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe ether is removed under reduced pressure

Sources & evidence

ORD record
ord-fb716bdc833f4ddaa22644b785cb7b8e
Source dataset
uspto-grants-1987_03
Patent number
US04654438

Reaction notes

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