Salicyl Alcohol → Diethyl 2-hydroxybenzylphosphonate

HRID 1640355Notes

Reaction equation

HRID 1640355 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]O.[P:10]([O:17]CC)([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]>CC1C=CC=CC=1C>[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 5146Salicyl AlcoholHCID 31215Triethyl phosphite

Product 1

HCID 23415580Diethyl 2-hydroxybenzylphosphonateYield 90%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

38.4 g of 2-hydroxybenzylalcohol from TOKYO KASEI KOGYO Co., Ltd. and 80 ml of o-xylene were put in a reaction reservoir having a mixer, a thermometer and a dropping funnel. Under a nitrogen stream, 62.8 g of triethyl phosphite were slowly dropped therein at 80° C., and the reaction therein is further performed for 1 hr at the same temperature. Then, the produced ethanol, o-xylene and unreacted triethyl phosphite were removed from the reaction by reduced-pressure distillation to prepare 66 g of 2-diethylhydroxybenzylphosphonate at a yield of 90%, having a boiling point of 120.0° C./1.5 mm Hg.

Workup

  1. customat 80° C., and the reaction
  2. customThen, the produced ethanol, o-xylene and unreacted triethyl phosphite were removed from the reaction by reduced-pressure distillation
  3. customto prepare 66 g of 2-diethylhydroxybenzylphosphonate at a yield of 90%

Sources & evidence

ORD record
ord-1882de1003c64074820bd835c4dc21df
Source dataset
uspto-grants-2012_02
Patent number
US08114563B2

Reaction notes

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