Dimethylformamide → 4-tert.-Butyl-2,6-dimethyl-3-hydroxyphenylacetyl chloride

HRID 2049138Notes

Reaction equation

HRID 2049138 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][C:13](O)=[O:14])=[C:7]([CH3:16])[C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2].CN(C)C=O.S(Cl)([Cl:25])=O>C1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([CH2:12][C:13]([Cl:25])=[O:14])=[C:7]([CH3:16])[C:6]=1[OH:17])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 203459052-(4-tert-Butyl-3-hydroxy-2,6-dimethylphenyl)acetic acid

Product 1

HCID 203458974-tert.-Butyl-2,6-dimethyl-3-hydroxyphenylacetyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

47.2 g (0.20 moles) of 4-t-butyl-2,6-dimethyl-3-hydroxyphenyl acetic acid, and 0.4 ml of dry N,N-dimethylformamide are dispersed in 325 ml of dry benzene. To this slurry was added dropwise with stirring under a nitrogen atmosphere 28.5 g (17.5 ml, 0.24 moles) of thionyl chloride at ambient temperature. The reaction mixture was allowed to stir for 16 hours, then evaporated under reduced pressure, yielding an orange-colored solid, which proved by analysis to be the desired acid chloride. The residue was dissolved in 500 ml of benzene, analyzed for chloride ion and used for subsequent reactions in solution.

Workup

  1. additionTo this slurry was added dropwise
  2. customevaporated under reduced pressure
  3. customyielding an orange-colored solid, which

Sources & evidence

ORD record
ord-b1efb26b7f85484f9764ddde52d97eb2
Source dataset
uspto-grants-1980_04
Patent number
US04196301

Reaction notes

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