Hydrochloric Acid → 2-Hydroxy-5-phenoxybenzaldehyde

HRID 722316Notes

Reaction equation

HRID 722316 reaction equation
C([Mg]Br)C.[O:5]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN(P(N(C)C)(N(C)C)=O)C.[CH2:30]=[O:31].Cl>C(OCC)C.C1(C)C=CC=CC=1>[O:5]([C:12]1[CH:13]=[C:14]([CH:30]=[O:31])[C:15]([OH:18])=[CH:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 12679HexamethylphosphoramideHCID 132544-PhenoxyphenolHCID 178418443HCID 178418443, compound

Product 1

HCID 149712582-Hydroxy-5-phenoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
80 °C

Procedure

Ethyl magnesium bromide (67.5 mL of an approximately 3.0 M solution in diethyl ether, 202.5 mmol) was added to toluene (50 mL). A solution of 4-phenoxyphenol (25.00 g, 134.26 mmol) in diethyl ether (35 mL) was added resulting in the evolution of gas. The reaction was heated to 80° C. causing distillation of the diethyl ether. Toluene (300 mL), HMPA (23.4 mL, 24.059 g, 134.26 mmol), and paraformaldehyde (10.07 g, 335.65 mmol) were added and the reaction was heated to 85° C. for 4 hours. The reaction was cooled to room temperature and was acidified with 2N HCl.

Workup

  1. customresulting in the evolution of gas
  2. distillationdistillation of the diethyl ether
  3. temperaturethe reaction was heated to 85° C. for 4 hours
  4. temperatureThe reaction was cooled to room temperature

Sources & evidence

ORD record
ord-5c634c65791e421f9504ccf65a4efcb1
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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