Hydrochloric Acid → HCID 12138346, compound

HRID 1271663Notes

Reaction equation

HRID 1271663 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([CH:30]=[C:31]([S:33][CH3:34])[CH:32]=1)[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[C:24]([S:26][CH3:27])[CH:23]=[C:22]([S:28][CH3:29])[CH:21]=2)[CH:17]=1)[C:11](OC)=[O:12].Cl>O1CCCC1>[CH3:34][S:33][C:31]1[CH:30]=[C:5]([CH:4]=[C:3]([S:2][CH3:1])[CH:32]=1)[CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[C:24]([S:26][CH3:27])[CH:23]=[C:22]([S:28][CH3:29])[CH:21]=2)[CH:17]=1)[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12138345HCID 12138345, compound

Product 1

HCID 12138346HCID 12138346, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To sodium dihydrobis(2-methoxyethoxy)aluminate (70% in toluene, 22.7 g, 0.078 mol), was added dropwise a solution of methyl 3,5-bis(3,5-dimethylthiobenzyloxy)benzoate (21.0 g) in tetrahydrofuran (180 ml) in a stream of nitrogen at 5–10° C. during 30 minutes. After completion of the addition, the mixture was stirred for 5 hours and then poured into 2 L of diluted hydrochloric acid, followed by extraction with 1 L of chloroform. The extract was evaporated to dryness, and the residue was purified by means of chromatography using chloroform as the developing solvent, giving 3,5-bis(3,5-dimethylthiobenzyloxy)benzyl alcohol. The yield was 17.5 g (85.6%).

Workup

  1. additionAfter completion of the addition
  2. extractionfollowed by extraction with 1 L of chloroform
  3. customThe extract was evaporated to dryness
  4. customthe residue was purified by means of chromatography

Sources & evidence

ORD record
ord-5217784bb4ba485bbf55b53e1dee9d92
Source dataset
uspto-grants-2007_04
Patent number
US07205428B2

Reaction notes

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