Water → HCID 59516424, compound

HRID 1160472Notes

Reaction equation

HRID 1160472 reaction equation
C([O:7][C:8]1[CH:9]=[C:10]([CH2:14][C@H:15]([O:20][CH:21]([CH3:23])[CH3:22])[C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:12][CH:13]=1)(=O)C(C)(C)C.S(=O)(=O)(O)O.C1(C)C=CC=CC=1.O>CO>[OH:7][C:8]1[CH:9]=[C:10]([CH2:14][C@H:15]([O:20][CH:21]([CH3:23])[CH3:22])[C:16]([O:18][CH3:19])=[O:17])[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 1140TolueneHCID 59516436HCID 59516436, compound

Product 1

HCID 59516424HCID 59516424, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl (2S)-3-(3-pivaloyloxyphenyl)-2-isopropoxypropionate (12.1 kg, 37.5 mol) was dissolved in methanol (49 L) and then cooled, followed by adding dropwise concentrated sulfuric acid (3 L) to the reaction mixture at an internal temperature of 8.8° C. After stirring the reaction mixture at 60° C. for 19 hours, toluene (121 L) and water (61 L) were added to the mixture for separating. The aqueous layer was again extracted with toluene (121 L). The organic layers were then combined. The resultant organic layer was washed with a 5% sodium bicarbonate aqueous solution (57 L) and with water (61 L) and then dried with anhydrous magnesium sulfate, followed by vacuum concentration to obtain 8.81 kg of the title compound in the form of oily matter (yield: 99%).

Workup

  1. temperaturecooled
  2. customfor separating
  3. extractionThe aqueous layer was again extracted with toluene (121 L)
  4. washThe resultant organic layer was washed with a 5% sodium bicarbonate aqueous solution (57 L) and with water (61 L)
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationfollowed by vacuum concentration

Sources & evidence

ORD record
ord-63d681c394fe419a97c847ecd66666c3
Source dataset
uspto-grants-2010_10
Patent number
US07816405B2

Reaction notes

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