Water → 3-Phenoxybenzyl alcohol

HRID 1284261Notes

Reaction equation

HRID 1284261 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(OCC)C>O1CCCC1>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 195393-Phenoxybenzoic acid

Product 1

HCID 262953-Phenoxybenzyl alcoholYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After stirring the reaction mixture for an additional 0.5 hour at 0°-5°C, a solution of 3860 grams (18 moles) of m-phenoxybenzoic acid in tetrahydrofuran was added dropwise over a 4 hour period while maintaining a reaction temperature of 0°-10°C. When the addition was complete, the reaction mixture was stirred for 12 hours at 20°C followed by 2 hours at 40°C. The reaction mixture was then transferred to a 10 gallon bottle containing 6 liters of water and 8 liters of diethyl ether. After mixing thoroughly, the aqueous layer was removed and the organic layer was extracted with water (1 × 4 liters), extracted with aqueous saturated sodium bicarbonate solution (1 × 4 liters), extracted with aqueous saturated sodium chloride solution (1 × 4 liters), dried over anhydrous potassium carbonate, filtered, and concentrated on a rotary evaporator. Short-path distillation gave 3000 grams (83% yield) of m-phenoxybenzyl alcohol, bp 135°-140°C/0.10 mm, n20D 1.5935.

Workup

  1. temperaturewhile maintaining a reaction temperature of 0°-10°C
  2. additionWhen the addition
  3. stirringthe reaction mixture was stirred for 12 hours at 20°C
  4. waitfollowed by 2 hours at 40°C
  5. additionAfter mixing thoroughly
  6. customthe aqueous layer was removed
  7. extractionthe organic layer was extracted with water (1 × 4 liters)
  8. extractionextracted with aqueous saturated sodium bicarbonate solution (1 × 4 liters)
  9. extractionextracted with aqueous saturated sodium chloride solution (1 × 4 liters)
  10. dry with materialdried over anhydrous potassium carbonate
  11. filtrationfiltered
  12. concentrationconcentrated on a rotary evaporator
  13. distillationShort-path distillation

Sources & evidence

ORD record
ord-9fad61c4c5e54e01852d188870c15165
Source dataset
uspto-grants-1976_08
Patent number
US03978140

Reaction notes

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