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

HRID 1288498Notes

Reaction equation

HRID 1288498 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-197eadfa0b0b4c659626dbb47569eac7
Source dataset
uspto-grants-1976_10
Patent number
US03988363

Reaction notes

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