Hydrochloric Acid → HCID 12138346, compound

HRID 987173Notes

Reaction equation

HRID 987173 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 2L of diluted hydrochloric acid, followed by extraction with 1L 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 1L of chloroform
  3. customThe extract was evaporated to dryness
  4. customthe residue was purified by means of chromatography

Sources & evidence

ORD record
ord-4b5a2d8060e9474fbe00751374cf9611
Source dataset
uspto-grants-2003_10
Patent number
US06630578B2

Reaction notes

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