Diethyl Ether → 3,4-Dibenzyloxybenzoic acid anhydride

HRID 280876Notes

Reaction equation

HRID 280876 reaction equation
CCOCC.[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:17]([OH:19])=[O:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:31]([O:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][C:47]=1[O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:42](Cl)=[O:43])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>N1C=CC=CC=1>[CH2:31]([O:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][C:47]=1[O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:42]([O:18][C:17](=[O:19])[C:16]1[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:14]([O:13][CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:15]=1)=[O:43])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 108541553,4-Bis(benzyloxy)benzoic acidHCID 110026733,4-Bis(benzyloxy)benzoyl chloride

Product 1

HCID 108868213,4-Dibenzyloxybenzoic acid anhydride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The mixture consisting of 1.5 liter of anhydrous ether, 290 cc of pyridine, 100.2 g of 3,4-dibenzyloxybenzoic acid and 105.7 g of 3,4-dibenzyloxybenzoic acid chloride is stirred for 24 hours at ambient temperature in a round-bottom flask provided with a drying tube. The mixture is then poured in 8 liters of ice water. After 45 min stirring the precipitate is filtered, washed with one liter of 0.1N iced hydrochloric acid, one liter of iced 0.1N Na2CO3, then one liter of ice water. The solid is solubilized in CHCl3 ; it is decanted, dried and evaporated and the anhydride is recrystallized in ethyl acetate. Yield 88%.

Workup

  1. customprovided with a drying tube
  2. stirringAfter 45 min stirring the precipitate
  3. filtrationis filtered
  4. washwashed with one liter of 0.1N iced hydrochloric acid, one liter of iced 0.1N Na2CO3
  5. customit is decanted
  6. customdried
  7. customevaporated
  8. customthe anhydride is recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-affac8597ae14c8e956d60699660b6fb
Source dataset
uspto-grants-1986_05
Patent number
US04591600

Reaction notes

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