Boron trifluoride etherate → 2-Nitrophenethyl alcohol

HRID 1284263Notes

Reaction equation

HRID 1284263 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13](O)=[O:14])([O-:5])=[O:4].B(F)(F)F.CCOCC>>[N+:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][OH:14])([O-:5])=[O:4]

Participants

4

Reactant 3

HCID 8000Boron trifluoride etherateHCID 77337(2-Nitrophenyl)acetic acidHCID 4311764Sodium borohydride

Product 1

HCID 270542-Nitrophenethyl alcoholYield 73.3%

Conditions

Temperature
0 °C

Procedure

A 22-liter, 4-necked glass reaction vessel equipped as described in Example 1 was charged with 624 grams (15.8 moles plus 5% excess) of sodium borohydride and 3620 grams (20 moles) of o-nitrophenylacetic acid and flushed for 0.5 hour with dry nitrogen. The reaction vessel was cooled to 0°C using an external dry ice/isopropyl alcohol bath as 10 liters of tetrahydrofuran was added dropwise over a 2 hour period. Boron trifluoride diethyl etherate (2.58 liters, 21 moles) was then added dropwise over a 4 hour period while maintaining a reaction temperature of 0°-10°C. The reaction mixture was then stirred for 12 hours at 20°-25°C. Isolation of the product as described in Example 1 gave 2450 grams (73% yield) of o-nitrophenethyl alcohol as a clear, light-orange liquid, bp 112°C/0.15 mm, n20D 1.5644.

Workup

  1. customA 22-liter, 4-necked glass reaction vessel
  2. customequipped
  3. customflushed for 0.5 hour with dry nitrogen
  4. additionwas added dropwise over a 2 hour period
  5. temperaturewhile maintaining a reaction temperature of 0°-10°C

Sources & evidence

ORD record
ord-5ca568a05017404aa5e6ae8a05432481
Source dataset
uspto-grants-1976_08
Patent number
US03978140

Reaction notes

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