Boron trifluoride etherate → 3-Phenoxybenzyl alcohol

HRID 1284262Notes

Reaction equation

HRID 1284262 reaction equation
[BH4-].[Na+].[O:3]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](O)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.B(F)(F)F.CCOCC>[Hg]>[O:3]([C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH2:13][OH:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 195393-Phenoxybenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 262953-Phenoxybenzyl alcoholYield 80%

Reagents, catalysts & solvents 1

HCID 23931MercuryCatalyst

Conditions

Temperature
20 °C

Procedure

A 500-milliliter, 4-necked glass reaction vessel equipped with a magnetic stirring bar, pressure-equalizing addition funnel, thermometer, and reflux condenser vented to a mercury bubbler was charged with 9.6 grams (0.248 mole plus 5% excess) of sodium borohydride and 64 grams (0.30 mole) of m-phenoxybenzoic acid and flushed 10 minutes with dry nitrogen. The reaction vessel was cooled in an external ice/water bath as 0.2 liter of tetrahydrofuran was added dropwise followed by 40.6 milliliters (0.33 mole) of boron trifluoride diethyl etherate over a 1 hour period while maintaining a temperature of 0°-10°C. The reaction mixture was then stirred for 12 hours at 20°C followed by 2 hours at 40°C. The product was isolated using a procedure similar to that described in Example 1 giving 48 grams (80% yield) of m-phenoxybenzyl alcohol, n20D 1.5935.

Workup

  1. customA 500-milliliter, 4-necked glass reaction vessel
  2. customequipped with a magnetic stirring bar, pressure-equalizing addition funnel
  3. temperaturethermometer, and reflux condenser
  4. customflushed 10 minutes with dry nitrogen
  5. temperatureThe reaction vessel was cooled in an external ice/water bath as 0.2 liter of tetrahydrofuran
  6. additionwas added dropwise
  7. temperaturewhile maintaining a temperature of 0°-10°C
  8. waitfollowed by 2 hours at 40°C
  9. customThe product was isolated

Sources & evidence

ORD record
ord-01ba2ead62ed4a8d902d3beb7c7f799e
Source dataset
uspto-grants-1976_08
Patent number
US03978140

Reaction notes

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