Salicyl Alcohol → (2-hydroxybenzyl)diphenylphosphine oxide

HRID 1731386Notes

Reaction equation

HRID 1731386 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].C([O:12][P:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C>O1CCCC1>[C:14]1([P:13]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[OH:9])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:12])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 5146Salicyl AlcoholHCID 69754Ethyl diphenylphosphinite

Product 1

HCID 796918(2-hydroxybenzyl)diphenylphosphine oxideYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a reactor equipped with a thermometer, a stirrer and a condenser were placed 99.2 g of o-(hydroxymethyl)phenol and 400 ml of tetrahydrofuran. They were made into a uniform solution. Thereto was added 184 g of ethyldiphenylphosphinite. The resulting mixture was subjected to reaction for 3 hr with heating and stirring. The reaction mixture was cooled and the resulting white crystal precipitate was separated by filtration and then dried to obtain 180 g of o-(diphenylphosphinylmethyl)phenol. Yield: 73% Melting point: 179° C.

Workup

  1. customIn a reactor equipped with a thermometer, a stirrer and a condenser
  2. customThe resulting mixture was subjected to reaction for 3 hr
  3. temperaturewith heating
  4. temperatureThe reaction mixture was cooled
  5. customthe resulting white crystal precipitate was separated by filtration
  6. customdried

Sources & evidence

ORD record
ord-5647367e0eba436fbcbd8afd303727e6
Source dataset
uspto-grants-1986_11
Patent number
US04621123

Reaction notes

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