Methanol → Methyl 3,3-dimethylpentanoate

HRID 425315Notes

Reaction equation

HRID 425315 reaction equation
[CH3:1][C:2](O)([CH2:4][CH3:5])[CH3:3].C(Cl)(Cl)=C.S(=O)(=O)(O)O.C[OH:17].C[CH2:19][O:20][CH2:21][CH3:22]>>[CH3:1][C:2]([CH3:3])([CH2:4][CH3:5])[CH2:22][C:21]([O:20][CH3:19])=[O:17]

Participants

6

Reactant 5

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 6366Vinylidene chlorideHCID 64052-Methyl-2-butanol

Product 1

HCID 3757207Methyl 3,3-dimethylpentanoate

Procedure

2-Methyl-2-butanol (480 mL, 4.4 mol) and vinylidene chloride (508 mL, 5.2 mol) were added to sulfuric acid (2 L) at 10° C. Methanol (1750 mL) was added slowly allowing exotherm to attain 40° C. and subsequently 60° C. for 15 minutes. The reaction mixture was cooled and poured into a stirred mixture of ether and ice water. The ethereal layer was washed with 1 N aqueous sodium hydroxide and brine, dried (magnesium sulfate), filtered, and concentrated in vacuo to afford methyl 3,3-dimethylpentanoate which was used in the subsequent step without further purification.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe ethereal layer was washed with 1 N aqueous sodium hydroxide and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-871fa3b0fbcc45088bbf2a4497775054
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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