Benzoyl chloride → 4-(Hydroxymethyl)phenyl benzoate

HRID 1841842Notes

Reaction equation

HRID 1841842 reaction equation
C(N([CH2:6][CH3:7])CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:17](=[O:20])([O-])[O-:18].[Na+].[Na+]>ClCCl>[C:17]([O:18][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][OH:15])=[CH:10][CH:11]=1)(=[O:20])[C:7]1[CH:6]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10340Sodium Carbonate

Product 1

HCID 131816394-(Hydroxymethyl)phenyl benzoateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(Hydroxymethyll)phenol (1.087 g, 8.77 mmol) and triethylamine (1.3 mL, 8.77 mmol) were dissolved in 25 mL of dichloromethane. The solution was shaken at 0° C. for 30 minutes. Benzoyl chloride (1 mL, 8.77 mmol) was added drop by drop and the resulting solution was shaken at 0° C. for 5 hours. Saturated aqueous solution of sodium carbonate (20 mL) was added three times. The organic phase was dried over magnesium sulfate, filtered, and the solvent was removed under reduced pressure, thus affording a yellowish solid that upon recrystallization from cyclohexane provided 1.600 g (70.16 mmol, yield=80%) of 4-(hydroxymethyl)phenyl benzoate.

Workup

  1. stirringthe resulting solution was shaken at 0° C. for 5 hours
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customthus affording a yellowish solid
  6. customthat upon recrystallization from cyclohexane

Sources & evidence

ORD record
ord-8d40d8eebbe8404f9e523490e623f467
Source dataset
uspto-grants-2015_02
Patent number
US08945522B2

Reaction notes

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