Lithium Hydroxide → ({[2-(1,3-Benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic Acid

HRID 603915Notes

Reaction equation

HRID 603915 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:18][S:19][CH2:20][C:21]([O:23]CC)=[O:22])[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[CH2:12][O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[Li+].[OH-]>O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:18][S:19][CH2:20][C:21]([OH:23])=[O:22])[O:15][CH2:14][C:13]([CH3:17])([CH3:16])[CH2:12][O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59197900Ethyl ({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate

Product 1

HCID 59197899({[2-(1,3-Benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl ({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate (Method 12) (14.2 g, 0.039 mol) was dissolved in THP (300 mL) and cooled to 0° C. LiOH (4.87 g, 0.12 mol) in water (100 mL) was added, and the mixture was given room temperature and stirred for 19 hours. The solvents were evaporated, the crude product was added water and extracted with diethyl ether. The aqueous layer was added 1M HCl until pH=3 and extracted twice with CH2Cl2. The combined CH2Cl2 layers were dried (Na2SO4) and concentrated under reduced pressure to afford the desired product.

Workup

  1. customwas given room temperature
  2. customThe solvents were evaporated
  3. additionthe crude product was added water
  4. extractionextracted with diethyl ether
  5. additionThe aqueous layer was added 1M HCl until pH=3
  6. extractionextracted twice with CH2Cl2
  7. dry with materialThe combined CH2Cl2 layers were dried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f1a9013a6d74f20a3f66234784ca979
Source dataset
uspto-grants-2011_03
Patent number
US07906502B2

Reaction notes

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