Hydrochloric Acid → 4-t-Butyl-2-(4-t-butylbenzoyl)benzoic acid

HRID 900389Notes

Reaction equation

HRID 900389 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[O:13])[O:11][C:9](=[O:10])[C:8]2=[CH:14][CH:15]=1)([CH3:4])([CH3:3])[CH3:2].[C:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC(Cl)C>[C:1]([C:5]1[CH:15]=[CH:14][C:8]([C:9]([OH:11])=[O:10])=[C:7]([C:12](=[O:13])[C:23]2[CH:24]=[CH:25][C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:21][CH:22]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7366Tert-ButylbenzeneHCID 1229304-tert-Butylphthalic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 77302724-t-Butyl-2-(4-t-butylbenzoyl)benzoic acidYield 54%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 500 ml three-necked flask, 36 g (176 mmole) of 4-t-butyl-phthalic anhydride, 27 g (200 mmole) of t-butylbenzene and 100 ml of dichloroethane were placed under a stream of argon and cooled to 0° C. To the obtained mixture, 56 g (420 mmole) of aluminum chloride was slowly added. After the addition was completed, the resultant mixture was stirred at the room temperature for one night. After the reaction was completed, ice was added slowly, and then concentrated hydrochloric acid was added. The formed precipitates were separated by filtration and washed well with water, and 32 g of the benzoic acid compound of the object compound was-obtained (the yield: 54%; a white powder).

Workup

  1. additionAfter the addition
  2. additionice was added slowly
  3. customThe formed precipitates
  4. customwere separated by filtration
  5. washwashed well with water, and 32 g of the benzoic acid compound of the object compound
  6. customwas-obtained (the yield: 54%

Sources & evidence

ORD record
ord-37d53c14ab19409e826753e5f9034555
Source dataset
uspto-grants-2008_04
Patent number
US07357991B2

Reaction notes

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